Isopropanol → 1-Phenylethanol, (R)-
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]=1Participants
3
Conditions
- Temperature
- 25 °C
Procedure
To the reaction solution obtained in (3) were added acetophenone (0.56 ml, 4.81 mmol) and 2-propanol (9.4 ml, 121 mmol), and the mixture was stirred at 25° C. for 24 hours. The reaction mixture was purified by means of Kugelrohr distillation to give (R)-1-phenylethanol (0.541 g, 92% yield). The asymmetric yield of the product was measured in a HPLC using a CHIRALCEL OD column (4.6×250 mm, Daicel Chemical Industries Ltd) and found to be not less than 99% e.e. In the table below, the results obtained by using a metal-ligand complex 4 (described on page 9800 of J. Am. Chem. Soc. 1993, 115, 9800-9801 and hereinafter referred to as the comparative compound) are also given for comparison.
Workup
- distillationThe reaction mixture was purified by means of Kugelrohr distillation
Sources & evidence
- ORD record
- ord-51eb4be6ae58423dbbb4c31184aeefdd
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07635776B2
Reaction notes
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