Acetophenone → 1-Phenylethanol, (R)-

HRID 1265423Notes

Reaction equation

HRID 1265423 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2]>CC(O)C>[C:4]1([C@H:1]([OH:3])[CH3:2])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 7410Acetophenone

Product 1

HCID 6375161-Phenylethanol, (R)-Yield 99.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Acetophenone (200 ml, 1.5 mol) was charged to the catalyst solution, followed by 2-propanol (0.5 l). The pressure was reduced (28.5 mmHg) and then a sodium 2-propoxide solution (120 ml of 0.1M solution in 2-propanol) was charged. The mixture was stirred at ambient temperature under nitrogen for 2.5 h, at hourly intervals the flask was back filled with nitrogen and sufficient 2-propanol charged to compensate for the volume removed by distillation. This gave (R)-1-phenylethanol Yield 99.6%, ee 82.9%. The turnover number, integrated over 1 h, was 454 h−1.

Workup

  1. additioncharged
  2. customremoved by distillation

Sources & evidence

ORD record
ord-5966315bb1234d9cb26a6b474f11b593
Source dataset
uspto-grants-2003_04
Patent number
US06545188B2

Reaction notes

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