p-Bromoacetophenone → (R)-1-(4-Bromophenyl)ethanol

HRID 324759Notes

Reaction equation

HRID 324759 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1.CC(C1C=CC(Br)=CC=1)=O.BrC1C=CC([C@@H](O)C)=CC=1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:10])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7466p-BromoacetophenoneHCID 953521-(4-Bromophenyl)ethanolHCID 2734890(S)-4-Bromo-alpha-methylbenzyl alcohol

Product 1

HCID 6950173(R)-1-(4-Bromophenyl)ethanolYield 57%

Procedure

As shown here, the biochemical conversion reaction of immobilized buckwheat protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 11 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (S)-1-(4-bromophenyl)ethanol to obtain 114 mg of (R)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e.

Sources & evidence

ORD record
ord-5816d348e29d46978f9c34b11d25b27b
Source dataset
uspto-grants-2001_04
Patent number
US06218581B1

Reaction notes

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