Dimethyl Sulfoxide → Benzenemethanol, alpha-ethenyl-, 1-acetate

HRID 1983976

Reaction equation

[CH:1]([CH:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].[C:11]([O-:14])(=[O:13])[CH3:12].[K+].CS(C)=O>O>[C:11]([O:14][CH:3]([CH:1]=[CH2:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:13])[CH3:12]

Participants

Conditions

Temperature: 40 °C

Procedure

In a one liter 3-neck round bottom flask equipped with a condenser, mechanical stirrer and thermometer, 108 grams (0.708 mol) of vinylbenzyl chloride (60/40 m-/p-) and 808 grams (0.815 mol) of potassium acetate were added, followed by 250 mLs of DMSO. The mixture was stirred at 40° C. for 48 hours. After allowing to cool to room temperature, the mixture was diluted with water and poured into a separatory funnel. The organic layer was separated, followed by an extraction of the aqueous layer with chloroform. The combined organic layer was then washed with water, dried over magnesium sulfate and placed on the rotary evaporator to remove the chloroform. 120 grams of the vinylbenzyl acetate product was recovered, to which 10 mg of MEHQ was added as an inhibitor.

Workup

customIn a one liter 3-neck round bottom flask equipped with a condenser, mechanical stirrer
temperatureto cool to room temperature
additionpoured into a separatory funnel
customThe organic layer was separated
extractionfollowed by an extraction of the aqueous layer with chloroform
washThe combined organic layer was then washed with water
dry with materialdried over magnesium sulfate
customplaced on the rotary evaporator
customto remove the chloroform
custom120 grams of the vinylbenzyl acetate product was recovered, to which 10 mg of MEHQ
additionwas added as an inhibitor

Sources & evidence

ORD record: ord-af0c0b19934242bfaa47c6791779d4f5
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544453B2

Linked notes

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