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Chemical Structure| 151-10-0 Chemical Structure| 151-10-0
Chemical Structure| 151-10-0

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CAS No.: 151-10-0

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Synonyms: Resorcinol dimethyl ether

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Product Details of 1,3-Dimethoxybenzene

CAS No. :151-10-0
Formula : C8H10O2
M.W : 138.16
SMILES Code : COC1=CC(OC)=CC=C1
Synonyms :
Resorcinol dimethyl ether
MDL No. :MFCD00008384
InChI Key :DPZNOMCNRMUKPS-UHFFFAOYSA-N
Pubchem ID :9025

Safety of 1,3-Dimethoxybenzene

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of 1,3-Dimethoxybenzene

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 151-10-0 ]

[ 151-10-0 ] Synthesis Path-Downstream   1~32

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  • [ 100-07-2 ]
  • [ 151-10-0 ]
  • [ 4038-15-7 ]
YieldReaction ConditionsOperation in experiment
aluminium trichloride; In hexane; dichloromethane; Step 1 1,3 dimethoxybenzene (57.0 grams, 0.41 mole) and p-anisoyl chloride (69.0 grams, 0.41 mole) were added to a reaction flask containing 1000 milliliters of methylene chloride. Aluminum chloride (61.0 grams, 0.45 mole) was added slowly and the resulting mixture was stirred for 4 hours under a nitrogen atmosphere. The reaction mixture was added to a 10 weight percent aqueous hydrochloric acid solution containing ice and stirred for about thirty minutes. The organic layer was separated and the aqueous layer was back extracted with 100 milliliters of methylene chloride. The organic portions were combined and washed with water and washed again with a dilute sodium hydroxide solution. The organic layer was dried over magnesium sulfate and the residual methylene chloride was removed under vacuum. The resulting oily product (96.0 grams) solidified upon standing. The solid was crushed, added to hexane, filtered, washed with hexane, and dried. The resulting product, 2,4,4'-trimethoxy-benzophenone was not purified further but used directly in the next step.
aluminium trichloride; In dichloromethane; Step 1 1,3-Dimethoxybenzene (13.8 grams, 0.1 mole) and p-anisoyl chloride (17 grams, 0.1 mole) were dissolved in 200 milliliters of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 grams) was added slowly to the reaction mixture over a period of 15 minutes with stirring. After stirring an additional 15 minutes, the contents of the flask were carefully poured into 200 milliliters of a mixture of ice and dilute hydrochloric acid. The organic fraction was separated and washed with water. The solvent was removed on a rotary evaporator leaving an oily product that solidified on standing. This solid was broken-up, washed with two 50 milliliter portions of pentane, and dried, yielding 2,4,4'-trimethoxybenzophenone.
1, 3-Dimethoxybenzene (13.8 g) and p-anisoyl chloride (17 g) were dissolved in a reaction flask containing 200 mL of methylene chloride and stirred at room temperature. Anhydrous aluminum chloride (15 g) was added slowly to the reaction mixture over a period of 15 minutes with stirring. After stirring an additional 15 minutes, the contents of the flask were carefully poured into 200 mL of a mixture of ice and dilute hydrochloric acid. The organic fraction was separated and washed with water. The solvent was removed on a rotary evaporator leaving an oily product that solidified on standing. This solid was broken-up, washed with two 50 rnL portions of pentane, and dried, yielding (2,4-dimethoxy- phenyl) - (4-methoxy-phenyl)-methanone.
  • 4
  • [ 3123-97-5 ]
  • [ 151-10-0 ]
  • [ 96818-19-8 ]
  • 5
  • [ 1835-65-0 ]
  • [ 151-10-0 ]
  • 2,5,6-Trifluoro-2',6'-dimethoxy-biphenyl-3,4-dicarbonitrile [ No CAS ]
  • 2,5,6-Trifluoro-2',4'-dimethoxy-biphenyl-3,4-dicarbonitrile [ No CAS ]
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  • [ 151-10-0 ]
  • [ 17715-69-4 ]
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  • [ 20469-65-2 ]
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  • [ 151-10-0 ]
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YieldReaction ConditionsOperation in experiment
52% EXAMPLES Production Example (A) Synthesis of Intermediate (A) [Show Image] (A-1) Synthesis of 1-bromo-2,6-dimethoxybenzene In the atmosphere of argon, 19.3g of 1,3-dimethoxybenzene and 500 mL of anhydrous diethyl ether were placed in a flask. 105 mL (1.6M) of a hexane solution of n-butyllithium was added, and the resulting reaction solution was stirred with heating for 4 hours. After cooling to room temperature while stirring, the reaction solution was cooled to -50C, followed by dropwise addition of 25g of bromine. Then, while heating the reaction solution to room temperature, stirring was conducted for 2 hours. Then, 300 mL of an aqueous 10% sodium thiosulfate solution was added, and the resulting mixture was stirred for 1 hour. The reaction solution was extracted with ether, and an aqueous phase was removed, and then, an organic phase was washed with saturated saline. The organic phase was dried with magnesium sulfate and concentrated. Residues were purified by means of silica gel column chromatography. The resulting crystals were washed with hexane, whereby 17.9g (yield: 52%) of white crystals of 1-bromo-2,6-dimethoxybenzene were obtained.
52% Under an argon atmosphere 1,3-dimethoxy benzene (19.3g), was charged with anhydrous diethyl ether (500mL) to the flask, added 1.6M n-butyl lithium in hexane solution (105mL), the reaction solution was stirred for 4 hours under heating. After cooling to room temperature with continuous stirring, cooled to -50 C., was added dropwise bromine (25 g). The reaction solution was stirred for 2 hours while warming to room temperature. 10% aqueous solution of sodium thiosulfate (300mL) added, and the mixture was stirred for 1 hour. The reaction solution was extracted with ether, after removing the aqueous layer, the organic layer was washed with saturated brine. The organic layer was dried over magnesium sulfate, concentrated, and the residue was purified by silica gel chromatography. The obtained crystals were washed with hexane to obtain Intermediate 14 (17.9g). The yield was 52%.
  • 10
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YieldReaction ConditionsOperation in experiment
74% With 4-chloromorpholine; ammonium peroxydisulfate; tris(bipyridine)ruthenium(II) dichloride hexahydrate; In acetonitrile; for 16.0h;Irradiation; General procedure: In a 5mL crimp cap vial 0.25mmol of the respective substrate, together with 0.3mmol (1.2equiv) of the N-chloramine or NCS, 0.3mmol (1.2equiv) (NH4)2S2O8, and 2mol% (0.005mmol) [Ru(bpy)3]Cl2×6H2O were dissolved in 2mL of MeCN/water 4:1. The reaction mixture was degassed by three cycles of freeze-pump-thaw and irradiated for 16h with blue LEDs (lambdamax=455nm). For GC analysis 500muL of the reaction mixture was added to 500muL of the standard solution (0.1M), anisole for dimethoxybenzene, toluene for anisole, mixed, filtered and submitted to GC analysis. For Tables 4 and 5: After the irradiation the internal standard (0.01mmol n-pentadecane) was added to the reaction and the reaction was immediately quenched with satd Na2CO3-solution and brine. The mixture was extracted with ethyl acetate and subjected to GC-FID analysis.
With N-chloro-succinimide; n-butyllithium; In 1,2-dimethoxyethane; (a) N-Chlorosuccimide Method To a solution of 1,3-dimethoxybenzene (13.8 g) in 1,2-dimethoxyethane (100 ml) is added 2.6M n-butyllithium (40 ml). After 40 minutes, N-chlorosuccinimide (13.5 g) is added and the reaction temperature is maintained below 55 C. by means of an ice-bath. After an additional 45 minutes, the reaction mixture is poured into water and extracted with ether. Evaporation of the organic extract affords an oil which is choromatographed on silica gel (125 g), eluding with 20% ether-hexane. Evaporation of the eluents affords an oil which crystallized on standing. Recrystallization from hexane gives 2-chloro-1,3-dimethoxybenzene, mp 62-64 C. ANALYSIS: Calculated for C8 H9 C102: 55.66%C, 5.25%H, 20.54%Cl. Found: 55.75%C, 5.20%H, 20.24%Cl.
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  • [ 42926-52-3 ]
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  • [ 42926-52-3 ]
  • [ 151-10-0 ]
  • [ 3113-27-7 ]
  • 15
  • [ 100-09-4 ]
  • [ 151-10-0 ]
  • [ 4038-15-7 ]
YieldReaction ConditionsOperation in experiment
73% With poly phosphoric acid; at 80℃; for 1.5h; General procedure: In order to prepare PPA (polyphosphoric acid), a mixture of H3PO4 (6.4 g) and P2O5 (11.5 g) in 150 mL beaker was stirred at 80 C for 15 min. 1-Bromo-3-methoxybenzene (9) (3.08 g,16.47 mmol) and 3,4-dimethoxybenzoic acid (7) (2 g, 10.98 mmol) were added to prepared PPA solution and the mixture was stirred with a glass stick at 80 C for 1.5 h. After the completion of the reaction, cold water was added to the reaction mixture and then the organic layer was extracted with EtOAc (3 150 mL). The combined organic phases were dried over Na2SO4 and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography with silica gel (30 g) by eluting with hexane:ethyl acetate (9:1). Recrystallization of the solid with hexane-ethyl acetate gave 2-bromo-4-methoxyphenyl)(3,4-dimethoxyphenyl)methanone (10) (2.32 g) as a white solid with 60% yield.
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  • [ 94088-46-7 ]
  • [ 151-10-0 ]
  • 2'-fluoro-2,4,6'-trimethoxybenzophenone-N-(2-methylethyl)ketimine [ No CAS ]
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  • [ 151-10-0 ]
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YieldReaction ConditionsOperation in experiment
With bismuth (III) nitrate pentahydrate; for 1.5h;Schlenk technique; Ionic liquid; Inert atmosphere; Heating; General procedure: The ionic liquid (3.5-4.0 mL) was charged into an oven-dried Schlenk tube under a nitrogen atmosphere and Bi(NO3)3·5H2O (1.5 mmol) was added. The respective aromatic compound (1 mmol) was then introduced into the Schlenk tube under a nitrogen atmosphere. The reaction mixture was magnetically stirred, initially at rt for about 10 min followed by stirring in a pre-heated oil bath at 80-85 C, until completion (as monitored by GC-MS). Once the reaction was over, the contents were cooled to rt and extracted with EtOAc-Hexane (2:3 vol/vol), until the final extraction did not show a spot corresponding to the starting material or to the product. The combined organic extracts were washed with 10% NaHCO3 solution, dried with MgSO4, and concentrated to give the crude product. Isomer distributions were determined by GC-MS, and/or by 1H NMR.
  • 22
  • [ 73183-34-3 ]
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YieldReaction ConditionsOperation in experiment
99% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 1,1'-di(pyridin-2-yl)-1,1',3,3'-tetrahydro-2,2'-bibenzo[d][1,3,2]diazaborole; at 100℃; for 16h;Inert atmosphere; The Examples milligrams Preparation of 3,5-dimethoxybenzene boronic acid pinacol ester, specifically including the steps of: nitrogenEnvironment, the reaction flask was added 1,3-dimethoxybenzene (69.1mg, 0.5mmol),CoupletBoronic acid pinacol ester(126.9mg, 0.5mmol, of formula (5)),Methoxy-1,5-cyclooctadiene iridium dimer(3.4mg, 0.005mmol, 1%, formula (6)),Borane pyridine ligands ago(4.0mg, 0.01mmol, 2%, of Formula (1))And cyclopentyl methyl ether(1mL, 1,3-dimethoxybenzene reaction concentration is 0.5mol / L),The reaction at 100 16h; the reaction was completed by rotary evaporation (20 ~ 40 ) removing the solvent (cyclopentyl methyl ether), was purified by columnChromatography (using 200-300 mesh size silica gel, substance to be purified by silica gel ratio of 50 to 100: 1, eluent stoneOleyl ether and ethyl acetate, the volume ratio 20 ~ 50: 1) to afford the product to give a colorless 3,5-dimethoxybenzene boronic acid pinacol ester solid(125mg, 99%),
90% With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole; at 100℃; for 3h;Schlenk technique; Inert atmosphere; Sealed tube; General procedure: B2pin2, [IrCl(COD)]2 (1.0 mol%), preligand 1 (2.0 mol%), and (hetero)arene (0.2 mmol, ifsolid) were placed in a dried Schlenk flask (15 mL in volume) equipped with a stirring bar. Afterevacuating and refilling the flask with dry nitrogen three times, (hetero)arene (0.2 mmol, if liquid)and methoxycyclopentane (CAPE, 0.5 mL) were added with syringes under a stream of nitrogen.The resulting mixture was stirred at the corresponding temperature for the assigned time. After cooling to room temperature, the reaction mixture was concentrated and then purified by columnchromatography on silica gel to give the target product (The spectra data for the borylated compoundscan be seen in the Supplementary Material).
68.4% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In cyclohexane; at 20℃;Inert atmosphere; 1523.6 mg (6 mmol) of pinacol diboronate (B2pin2), 132.6 mg of [Ir (0 Torr) (COD)] and 107.4 mg (0.30 mmol) of 4,4-di-tert-butyl linkage Into 15 mL of cyclohexane, add dtbpy, protect with N2, stir at room temperature, and add 1.22 mL of 1,3-dimethoxybenzene while stirring. Stir the reaction for 10 h. Evaporate the solvent and purify by column chromatography. Petroleum ether: Elution with ethyl acetate (V:V=5:1), dried to give 1083.4 mg of compound 3 with a yield of 68.4%.
References: [1]Patent: CN104725409,2016,B .Location in patent: Paragraph 0036; 0037; 0040.
[2]Journal of the American Chemical Society,2015,vol. 137,p. 8058 - 8061.
[3]Research on Chemical Intermediates,2013,vol. 39,p. 1917 - 1926.
[4]Molecules,2019,vol. 24.
[5]Organic Letters,2019,vol. 21,p. 6347 - 6351.
[6]Journal of the American Chemical Society,2015,vol. 137,p. 5193 - 5198.
[7]Chemistry - A European Journal,2017,vol. 23,p. 6282 - 6285.
[8]Patent: CN108003001,2018,A .Location in patent: Paragraph 0027; 0034.
[9]Tetrahedron,2008,vol. 64,p. 6824 - 6830.
[10]Organic Letters,2007,vol. 9,p. 757 - 760.
[11]Organic Letters,2007,vol. 9,p. 761 - 764.
[12]Journal of the American Chemical Society,2007,vol. 129,p. 15434 - 15435.
[13]Synlett,2009,p. 147 - 150.
[14]Tetrahedron Letters,2010,vol. 51,p. 2690 - 2692.
[15]Journal of the American Chemical Society,2010,vol. 132,p. 11389 - 11391.
[16]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 861 - 864.
[17]Organic Letters,2010,vol. 12,p. 5700 - 5703.
[18]Angewandte Chemie - International Edition,2011,vol. 50,p. 519 - 522.
[19]Angewandte Chemie - International Edition,2012,vol. 51,p. 536 - 539.
[20]Journal of the American Chemical Society,2012,vol. 134,p. 2528 - 2531.
[21]Angewandte Chemie - International Edition,2013,vol. 52,p. 933 - 937.
    Angew. Chem.,2012,vol. 125,p. 967 - 971,5.
[22]Organic Letters,2013,vol. 15,p. 140 - 143.
[23]Chemistry - A European Journal,2014,vol. 20,p. 11680 - 11684,5.
[24]Chemical Communications,2019,vol. 55,p. 2023 - 2026.
[25]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5703 - 5707.
[26]Journal of Organic Chemistry,2020,vol. 85,p. 3596 - 3604.
  • 23
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  • 4-methoxy-<i>trans</i>(?)-cinnamic acid [ No CAS ]
  • [ 185342-88-5 ]
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  • [ 151-10-0 ]
  • [ 3153-72-8 ]
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  • [ 151-10-0 ]
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  • 26
  • [ 151-10-0 ]
  • [ 117902-15-5 ]
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  • [ 151-10-0 ]
  • 2-<4-methoxy-benzoyl>-benzoyl chloride [ No CAS ]
  • [ 145069-56-3 ]
  • 28
  • [ 151-10-0 ]
  • 2-<4-methoxy-benzoyl>-benzoyl chloride [ No CAS ]
  • [ 16932-45-9 ]
  • 29
  • [ 558-13-4 ]
  • [ 151-10-0 ]
  • [ 16932-45-9 ]
YieldReaction ConditionsOperation in experiment
57% With n-butyllithium; In diethyl ether; hexane; water; REFERENCE EXAMPLE 3(1) In a solution of 1,3-dimethoxybenzene (3.0 g, 21.7 mmol) dissolved in diethyl ether (90 ml), a 1.65M solution of n-butyl lithium in n-hexane (19.8 ml, 32.7 mmol of n-butyl lithium) was added at room temperature, and a reaction mixture was heated to reflux for 4 hours. After cooling the reaction mixture to 0 C., a solution of carbon tetrabromide (15.8 g, 47.7 mmol) in diethyl ether (60 ml) was added to the mixture, and stirred at room temperature for 20 hours. A small amount of water was added to the reaction mixture, and then the reaction mixture was diluted with ethyl acetate (90 ml). The organic layer was washed with water and dried over anhydrous magnesium sulfate. Thereafter, the solvent was evaporated off, and the residue was purified by column chromatography to obtain 1-bromo-2,6-dimethoxybenzene (2.70 g). Yield, 57%. Elementary analysis: C8 H9 O2 Br Calculated: C, 44.23%; H. 4.15% Found: C, 44.02%; H. 4.23%.
  • 30
  • [ 116-16-5 ]
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YieldReaction ConditionsOperation in experiment
50% With n-butyllithium; In hexane; water; (e) Hexachloroacetone Method To a solution of 1,3-dimethoxybenzene (13.8 g) in dry ether (50 ml, freshly distilled from sodium benzophenone ketyl) is added dropwise 2.4M n-butyllithium (50 ml) at 5 C. over five minutes. After the addition is complete, the mixture is heated under reflux for two and one-half hours and then cooled to -65 C. To the cooled mixture is added dropwise a solution of hexachloroacetone (19.8 ml) in dry ether (50 ml) over one hour. The reaction mixture is allowed to warm to 0 C. and after one hour, water (50 ml) is added and the combined aqueous phases are extracted with ether. The combined ether fractions are dried over anhydrous magnesium sulfate and filtered. The filtrate is washed with 15% sodium sulfate solution, dried over anhydrous magnesium sulfate, filtered and evaporated. Trituration of the residue with hexane (41 ml) affords 2-chloro-1,3-dimethoxybenzene (8.6 g, 50%) as a gum. The gas-liquid chromatogram of the gum showed that it contained predominantly the desired 2-chloro compound. STR1
  • 31
  • [ 2785-97-9 ]
  • [ 151-10-0 ]
  • [ 7051-15-2 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; In 1,2-dimethoxyethane; (b) Chlorine Method Gaseous chlorine is condensed in a receptacle immersed in a dry ice-acetone bath until 2.5 ml is collected. The bath is removed and the chlorine is allowed to evaporate into a solution of [2,6-dimethoxyphenyl]lithium in 1,2-dimethoxyethane, prepared by adding 2.6M n-butyllithium (10 ml) to 1,3-dimethoxybenzene (6.9 g) dissolved in dimethoxyethane (50 ml) maintained at less than 50 C. by means of an ice-bath and permitting the resulting solution to stand for 40 minutes. After one hour, the reaction mixture is poured into water and extracted with ether. The ethereal extracts are dried, filtered and evaporated to afford an oil. A comparison of the proton magnetic resonance spectrum of the oil with that of authentic 2-chloro-1,3-dimethoxybenzene prepared by Method (a) indicated that the reaction product contained 62% of the 2-chloro compound.
  • 32
  • [ 67-72-1 ]
  • [ 151-10-0 ]
  • [ 7051-15-2 ]
YieldReaction ConditionsOperation in experiment
71.5% With n-butyllithium; In hexane; water; To a solution of 1,3-dimethoxybenzene (13.8 g) in dry ether (50 ml, freshly distilled from sodium benzophenone ketyl) is added dropwise 2.4M n-butyllithium (50 ml) at 5 C. over five minutes. After the addition is complete, the mixture is heated under reflux for two and one-half hours and then cooled to -2 C. To the cooled mixture is added dropwise a solution of hexachloroethane (30.9 g) in dry ether (80 ml) over 23 minutes, during which time the reaction temperature increased to 14 C. After this addition is complete, the reaction mixture is allowed to warm to room temperature and is stirred at room temperature overnight. The reaction mixture is cooled to 5 C. and water (50 ml) is added. The layers are separated and the ether layer is washed with water (50 ml). The aqueous phase is extracted with ether (50 ml) and the combined organic extracts are dried over anhydrous magnesium sulfate, filtered and evaporated. Recrystallization of the residue from hexane (60 ml) yields 2-chloro-1,3-dimethoxybenzene (12.3 g, 71.5%), mp 71-73 C. (reported mp 69-71 C., P. Kovacic and M. E. Kurtz, ibid. page 2465).
 

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