Hydrochloric Acid → 2-Chloro-1-phenylethanol, (+)-
Reaction equation
C([O:6][C@@H:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:8][Cl:9])(=O)CCC.Cl>>[Cl:9][CH2:8][C@H:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:6]Participants
Procedure
Sixteen grammes of enzyme (produced by Amano pharmaceutical Co. Ltd., Lipase "Amano CES"), 7.9g (0.05mol) of (R,S)-2-chloro-1-phenylethanol and 17.8g (0.059mol) of tributyrin were charged into three-necked flask and reacted with stirring for 16days at 35° C. After the reaction was stopped, the enzyme was removed by filtration, the filtrate was concentrated by distillation under reduced pressure, and the desired compounds were isolated by column chromatography. As the result, 4.0g of (R)-2-chloro-1-phenylethanol (yield: 50%, 58% ee) and (S)-2-chloro-1-phenylethyl butyrate were obtained. The obtained (S)-2-chloro-1-phenylethyl butyrate was hydrolyzed in an acidic solution of hydro chloric acid, and (S)-2-chloro-1-phenylethanol (yield: 23%, >99% ee) was obtained. Optical purity of the obtained compounds was determined by HPLC of optical resolution.
Sources & evidence
- ORD record
- ord-58c8239059cb4a898f83c7f2d002efee
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04962031
Reaction notes
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