Acetophenone → 1-Phenylethanol, (R)-

HRID 842337Notes

Reaction equation

HRID 842337 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 7410Acetophenone2×

Product 1

HCID 6375161-Phenylethanol, (R)-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The acetophenone was added to the catalyst solution. The mixture was stirred at ambient temperature for 1 h. Sodium 2-propoxide (0.25 ml of freshly prepared 0.1M solution in 2-propanol) was added. The mixture was stirred for 2 h and sampled; 57% of the acetophenone had reacted to give (R)-1-phenylethanol of 79% ee. The turnover number, integrated over 1 h, was 241 h−1.

Workup

  1. stirringThe mixture was stirred for 2 h
  2. aliquotsampled

Sources & evidence

ORD record
ord-316e21af17634c70aa631d483b60a5ba
Source dataset
uspto-grants-2002_04
Patent number
US06372931B1

Reaction notes

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