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[ CAS No. 167678-46-8 ] {[proInfo.proName]}

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Chemical Structure| 167678-46-8
Chemical Structure| 167678-46-8
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Product Details of [ 167678-46-8 ]

CAS No. :167678-46-8 MDL No. :MFCD02094037
Formula : C10H9ClO3 Boiling Point : -
Linear Structure Formula :- InChI Key :COLDUSGLGQXXEJ-UHFFFAOYSA-N
M.W : 212.63 Pubchem ID :7010345
Synonyms :

Safety of [ 167678-46-8 ]

Signal Word:Danger Class:8
Precautionary Statements:P234-P260-P264-P272-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P390-P405-P406-P501 UN#:3261
Hazard Statements:H290-H314-H317 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 167678-46-8 ]

* 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 [ 167678-46-8 ]

[ 167678-46-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 168899-58-9 ]
  • [ 167678-46-8 ]
YieldReaction ConditionsOperation in experiment
95.5% With thionyl chloride; at 80 - 170℃; for 2h; In einem Kolben werden unter Stickstoff 100,0 g Thionylchlorid vorgelegt und auf 60C aufgeheizt. Dazu tropft man eine 170C hei?e Schmelze von 100,0 g 3-Acetoxy-2-methylbenzoes?ure (AMBS) in einer Stunde zu. Die Reaktion setzt unter Gasentwicklung (SO2, HCl) sofort ein. Nach Beendigung der Zugabe wird innerhalb einer Stunde zum Rückfluss (80C) erhitzt und bei dieser Temperatur bis zum Abklingen der Gasentwicklung (ca. 1 h) gerührt. Die L?sung wird unter Stickstoff auf ca. 50C abgekühlt und der Rückflusskühler durch eine Vigreux-Kolonne ersetzt. Es werden bei Normaldruck (Sumpf bis 170C) 31,9 g Thionylchlorid abdestilliert und der zurückbleibende Sumpf im Vakuum (15 mbar) fraktioniert. Man erh?lt als Destillat 103,8 g 3-Acetoxy-2-methylbenzoylchlorid (98,5 %). Das entspricht 95,5 % d.Th.
91% With thionyl chloride; In xylene; at 75 - 108℃; for 4h; In einem Kolben werden unter Stickstoff in 140,0 g Xylol 60,0 g 3-Acetoxy-2-methylbenzoes?ure suspendiert. Die Suspension wird auf 70C aufgeheizt und 42,9 g Thionylchlorid zugetropft. Man heizt weiter auf. Bei ca. 75C setzt eine lebhafte Gasentwicklung (SO2, HCl) ein. Die Sumpftemperatur steigt kontinuierlich an und erreicht nach ca. 4 h 108C. Die L?sung wird unter Stickstoff auf ca. 50C abgekühlt und der Rückflusskühler durch eine Vigreux-Kolonne ersetzt. Es werden bei Normaldruck und sp?ter im Vakuum erst Xylol und Thionylchloridreste und dann das Produkt überdestilliert. Das Produkt destilliert bei 15 mbar und 147,0 - 148,0C über. Man erh?lt 59,6 g 3-Acetoxy-2-methylbenzoylchlorid (97,3 %). Das entspricht 91,0 % d.Th.
82.3% With thionyl chloride; In tert-butyl methyl ether; N,N-dimethyl-formamide; at 20℃; for 19h; A 22 L reactor was purged with nitrogen and charged with recrystallized <strong>[168899-58-9]3-acetoxy-2-methylbenzoic acid</strong> (3000 g), MTBE (12000 ml), and dimethylformamide (60 ml). The reactor contents were stirred to give a homogeneous mixture. Thionyl chloride (1350 ml) was added to the reactor. This reaction mixture was stirred at ambient temperature for 19 hours. (Generally no more than 3 hours are required for complete reaction, but the mixture can be held longer for convenience). The reaction solution was transferred to a Büchi rotovap, and the reactor was rinsed with toluene (1500 ml). The solution was concentrated as far as possible, maintaining the bath temperature at 40 - 50 C. Toluene (6000 ml) was added to this concentrated solution. The toluene was distilled by rotovap to drive off excess thionyl chloride. The concentrate was transferred back to the 22 L reactor, and the Büchi flask was rinsed with heptane (6000 ml). The heptane mixture was cooled to <5 C under nitrogen. After holding the crystallization mixture at <5 C for > 30 minutes, the mixture was filtered, and the filter cake was washed with chilled heptane (1500 ml, <5 C). The filter cake was dried in a vacuum oven at 15- 20 C and ≥28 mm Hg for 24 hours, giving a tan, granular solid. Theoretical yield: 3285 g. Actual weight produced: 2704 g (82.3%). HPLC assay 97.51%; 1H NMR δ 8.1 (d, 1H), 7.4 (overlapping m, 2H), 2.4 (s, 6H).
With thionyl chloride; 1b) Preparation of 3-acetoxy-2-methylbenzoyl chloride 31.1 g (0.16 mol) of the crude <strong>[168899-58-9]3-acetoxy-2-methylbenzoic acid</strong> (95% as obtained in Example 1a) and 36.0 g (0.30 mol) of thionyl chloride are initially introduced into a 250 ml four-necked flask which is equipped with a thermometer, reflux condenser and magnetic stirrer. The mixture is stirred and heated to reflux. The gases formed (HCl, SO2) are passed into aqueous sodium hydroxide solution. When the evolution of gas subsides, the excess thionyl chloride is distilled off. It can be reused for further reactions. The residue is distilled over a distillation bridge at 119 to 122 C. and 3 mbar. 25.6 g of 3-acetoxy-2-methylbenzoyl chloride are obtained in a purity of 98.5% (determined by GC analysis as methyl 3-acetoxy-2-methylbenzoate).
With thionyl chloride; In dichloromethane; at 20℃; for 18h; To a solution of the above benzoic acid (15.54 g, 80.00 mmol) in anhydrous DCM (100 ml) in a 500 ml round bottom flask was added 10 ml of thionyl chloride and 1 drop of anhydrous DMF. The teaction mixture was stirred overnight at room temperature. The solvent and excess thionyl chloride were removed under vacuum to give the product SKC-0l-048. SKC-01-048 was used without further purification in the next step.

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