Reaction equation
C([O:4][CH:5]([CH:12]=[CH2:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=O)C.[OH-].[Na+].C(O)C>COC1C=CC(O)=CC=1.O>[CH:12]([CH:5]([OH:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
120 grams (0.6876 mol) of vinylbenzyl acetate, inhibited with 10 mg of MEHQ were added to a one liter 3-neck round bottom flask equipped with a condenser, mechanical stirrer and thermometer, followed by 50 grams (1.25 mol) of sodium hydroxide. 50 mL of water and 300 mL of ethanol were then added and the contents of the flask heated at reflux (65° C.) for 2 hours. After the mixture was allowed to cool to room temperature, water was added. The content of the flask was poured into a separatory funnel and extracted with chloroform several times. The chloroform extract was subsequently washed several times with water and dried over magnesium sulfate. Removal of the chloroform on the rotary evaporator afforded 83 grams of the vinylbenzyl alcohol product (95% yield). The purification was accomplished by vacuum distillation.
Workup
- additionwere added to a one liter 3-neck round bottom flask
- customequipped with a condenser, mechanical stirrer
- temperaturethe contents of the flask heated
- temperatureto cool to room temperature
- additionThe content of the flask was poured into a separatory funnel
- extractionextracted with chloroform several times
- extractionThe chloroform extract
- dry with materialdried over magnesium sulfate
- customRemoval of the chloroform
- customon the rotary evaporator
Sources & evidence
- ORD record
- ord-4c66511c7ff14b63905c91ffc415ca9e
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07544453B2
Linked notes
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