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Chemical Structure| 622-08-2 Chemical Structure| 622-08-2
Chemical Structure| 622-08-2

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CAS No.: 622-08-2

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Product Details of 2-(Benzyloxy)ethanol

CAS No. :622-08-2
Formula : C9H12O2
M.W : 152.19
SMILES Code : OCCOCC1=CC=CC=C1
MDL No. :MFCD00002868
InChI Key :CUZKCNWZBXLAJX-UHFFFAOYSA-N
Pubchem ID :12141

Safety of 2-(Benzyloxy)ethanol

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501

Application In Synthesis of 2-(Benzyloxy)ethanol

* 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 [ 622-08-2 ]

[ 622-08-2 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 13220-33-2 ]
  • [ 622-08-2 ]
  • [ 2902-98-9 ]
  • 1-methyl-3-[2,2-diphenyl-2-(2-benzyloxyethoxy)acetoxy]pyrrolidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; Preparation 1 A mixture of chlorodiphenylacetyl chloride (20 g), <strong>[13220-33-2]1-methyl-3-pyrrolidinol</strong> (7.6 g), and pyridine (35 g) is kept at room temperature for two hours. After adding 45 g of 2-benzyloxyethanol, the mixture is refluxed gently for 18 hours. Excess pyridine and benzyloxyethanol are distilled off under reduced pressure, the residue is dissolved in ether and washed twice with water. The organic phase is dried over magnesium sulfate (MgSO4), filtered and the filtrate evaporated to dryness. Chromatography of the residue on the silica gel with ethyl acetate-hexane-triethylamine (50:50:1) as eluent affords 18 g of 1-methyl-3-[2,2-diphenyl-2-(2-benzyloxyethoxy)acetoxy]pyrrolidine as an oil.
  • 2
  • [ 59237-53-5 ]
  • [ 622-08-2 ]
  • C16H16N2O6 [ No CAS ]
  • C24H24N2O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 25℃; for 6h; 11231] To a solution of 643-1 (1.5 g, 6.9 mmol) in DMF (20 mL) was added 2- benzyloxyl ethanol (6.3 g, 41 mmol) at 25 °C. The solution wras stirred for 6 h and then poured into 0 (20 mL). The mixture was extracted with EA (2 x 40 mL). The combined organic phase was washed with brine, dried over anhydrous Na^SC^ and concentrated under reduced pressure. The residue was purified by column chromatography using 5-10percent EA in PE as the eluent to give a mixture of 643-2 and 643-2 A ( 1 .50 g).
  • 3
  • [ 59237-53-5 ]
  • [ 622-08-2 ]
  • C16H18N2O4 [ No CAS ]
  • C24H26N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
11231] To a solution of 643-1 (1.5 g, 6.9 mmol) in DMF (20 mL) was added 2- benzyloxyl ethanol (6.3 g, 41 mmol) at 25 °C. The solution wras stirred for 6 h and then poured into 0 (20 mL). The mixture was extracted with EA (2 x 40 mL). The combined organic phase was washed with brine, dried over anhydrous Na^SC^ and concentrated under reduced pressure. The residue was purified by column chromatography using 5-10percent EA in PE as the eluent to give a mixture of 643-2 and 643-2 A ( 1 .50 g). [1232] To a solution of 643-2A and 643-2 A (1.50 g. crude mixture) in EtOI I/I I20 (20/1 OmL) were added Fe ( 1 .5 g. 26.7 mmol) and NH4C1 (1 .5 g, 28 mmol) at 25 °C. The solution was heated to 80 °C and stirred for 2 h. The mixture was filtered, and the filtrate was concentrated to give a mixture of 643-3 and 643-3A ( 1.20 g, crude). The products were used for the next step without further purification.
  • 4
  • [ 59237-53-5 ]
  • [ 622-08-2 ]
  • C8H9NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
11231] To a solution of 643-1 (1.5 g, 6.9 mmol) in DMF (20 mL) was added 2- benzyloxyl ethanol (6.3 g, 41 mmol) at 25 °C. The solution wras stirred for 6 h and then poured into 0 (20 mL). The mixture was extracted with EA (2 x 40 mL). The combined organic phase was washed with brine, dried over anhydrous Na^SC^ and concentrated under reduced pressure. The residue was purified by column chromatography using 5-10percent EA in PE as the eluent to give a mixture of 643-2 and 643-2 A ( 1 .50 g). [1232] To a solution of 643-2A and 643-2 A (1.50 g. crude mixture) in EtOI I/I I20 (20/1 OmL) were added Fe ( 1 .5 g. 26.7 mmol) and NH4C1 (1 .5 g, 28 mmol) at 25 °C. The solution was heated to 80 °C and stirred for 2 h. The mixture was filtered, and the filtrate was concentrated to give a mixture of 643-3 and 643-3A ( 1.20 g, crude). The products were used for the next step without further purification.[1233] A mixture of 643-3 and 643-3A (1.2 g, crude) in H2S04/H20 (1 : 1 ) (l OmL) was cooled to -5 °C. NaN02 (376 mg, 5.45 mmol) was added in portions at -5 °C. The solution wras stirred at -5 °C for 0.5 h. The solution was heated to 120 °C. After stirring 0.5 h at 120 °C, the solution was poured into ice water (20 mL) and extracted with EA (2 x 20 mL). The organic phase was concentrated at low pressure. The residue was purified by chromatography to give 643-4 (0.3 g, crude).
  • 5
  • [ 84547-84-2 ]
  • [ 622-08-2 ]
  • 4-(2-(benzyloxy)ethoxy)-1-methyl-1H-pyrazole-5-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
23.74% With caesium carbonate; copper dichloride; at 130℃;Inert atmosphere; To a stirred mixture of 4-bromo-l-methyl-lH-pyrazole-5-carboxylic acid (60 g, 292.67 mmol, 1 equiv) in 2-(benzyloxy)ethan-l-ol (300 mL) were added CS2CO3 (286.1 g, 878.00 mmol, 3.00 equiv) and CuCh (3.9 g, 29.27 mmol, 0.10 equiv). The resulting mixture was stirred for overnight at 130 C under nitrogen atmosphere. The reaction was quenched with water and extracted with EtOAc. The aqueous phase was acidified to pH 2 with cone. HC1 and the resulting mixture was extracted with EtOAc. The combined organic layers were concentrated under reduced pressure. The residue was purified by reverse flashchromatography under the following conditions: column, Cl 8 silica gel; mobile phase, MeCN in water, 0% to 35% gradient in 25 min; detector, UV 254 nm to give (19.2 g, 23.74%) of the title compound as a white solid. LC-MS: (ES, m/z): [M+H]+277.
  • 6
  • [ 622-08-2 ]
  • [ 64224-60-8 ]
  • 5-(2-(benzyloxy)ethoxy)pyrimidine-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With potassium carbonate; copper(ll) bromide; at 100℃;Inert atmosphere; To a stirred solution of <strong>[64224-60-8]5-bromopyrimidine-4-carboxylic acid</strong> (4.3 g, 21.183 mmol, 1 equiv) and 2-(benzyloxy)ethan-l-ol (25 mL) were added K2CO3 (8.78 g, 63.548 mmol, 3 equiv) and CuBr2 (0.95 g, 4.237 mmol, 0.2 equiv) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for overnight at 100 C under nitrogen atmosphere. The mixture was acidified to pH 5 with HC1 (aq.) and extracted with EA. The residue was purified by silica gel column chromatography, eluted with CH2CI2 / MeOH (10: 1) to afford PH-IDE-0637-1 (1.0 g, 17 %) as a white solid.
 

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