p-Bromoacetophenone → (S)-4-Bromo-alpha-methylbenzyl alcohol

HRID 324749Notes

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

Reactant 3

HCID 7466p-Bromoacetophenone

HCID 953521-(4-Bromophenyl)ethanol

HCID 6950173(R)-1-(4-Bromophenyl)ethanol

Product 1

HCID 2734890(S)-4-Bromo-alpha-methylbenzyl alcoholYield 57%

Procedure

As shown here, the biochemical conversion reaction of immobilized green pea protein for the substrate (±)-1-(4-bromophenyl)ethanol (200 mg) requires 8 days by going through bioconversion to 4-bromoacetophenone accompanying sterically selective oxidation of (R)-1-(4-bromophenyl)ethanol to obtain 114 mg of (S)-1-(4-bromophenyl)ethanol at a yield of 57%. Optical purity was obtained at 88% e.e. The reaction course and time at completion of reaction were determined by GC using the Hitachi Model G-3500 gas chromatograph under conditions consisting of carrier gas: He at 0.48 ml/min, split ratio: 1/55, oven temperature: 150° C., inlet temperature: 250° C., outlet temperature: 250° C., pressure: 136, flow rate value: 42, analytical column: TC-5HT 0.25 mm I.D.×30M df (GL Science).

Sources & evidence

ORD record: ord-6d592d36f9614b30912d0e74865dc794
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218581B1

Reaction notes

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