Benzene → 1-Phenylethanol
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C1C=CC=CC=1.Cl>O1CCCC1>[C:4]1([CH:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
Under an atmosphere of nitrogen, 1.80 ml of a 0.99 M solution of acetophenone in tetrahydrofuran was added to the solution of reagent (A), obtained in Example 1, and the mixture stirred at 30° C. for 24 hours. The reaction mixture was poured into a mixture of 15 ml of benzene and 10 ml of 2 M hydrochloric acid, extracted with benzene, and the extract was washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by distillation in vacuo (130°-135° C./25 mmHg) to give 185 mg of 1-phenylethanol, and an additional purification was carried out by a fractional gas chromatography to give 1-phenylethanol having the following optical rotation:
Workup
- customobtained in Example 1
- extractionextracted with benzene
- washthe extract was washed with water
- dry with materialdried over sodium sulphate
- concentrationconcentrated under reduced pressure
- distillationThe residue was purified by distillation in vacuo (130°-135° C./25 mmHg)
Sources & evidence
- ORD record
- ord-2d4ee0aab4e4472ebd9a3f009cf36972
- Source dataset
- uspto-grants-1981_08
- Patent number
- US04284581
Reaction notes
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