2-Acetylnaphthalene → (S)-(-)-1-(2-Naphthyl)ethanol

HRID 324754

Reaction equation

HRID 324754 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([OH:13])[CH3:12].CC(C1C=CC2C(=CC=CC=2)C=1)=O.C1C2C(=CC=CC=2)C=CC=1[C@H](O)C>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C@@H:11]([OH:13])[CH3:12]

Participants

4

Reactant 3

HCID 71222-AcetylnaphthaleneHCID 98243alpha-Methylnaphthalene-2-methanolHCID 6976569(R)-(+)-1-(2-Naphthyl)ethanol

Product 1

HCID 6976568(S)-(-)-1-(2-Naphthyl)ethanolYield 50%

Procedure

As shown here, the biochemical conversion reaction of immobilized green pea protein for the substrate 1-(2-naphthyl)ethanol (201 mg) requires 4 days by going through bioconversion to 2-acetonaphthone accompanying sterically selective oxidation of (R)-1-(2-naphthyl)ethanol to obtain 100 mg of (S)-1-(2-naphthyl)ethanol at a yield of 50% at an optical purity of 99% e.e. or higher (see FIG. 1).

Sources & evidence

ORD record
ord-7b35a6765154448fa7d62659ae817dc6
Source dataset
uspto-grants-2001_04
Patent number
US06218581B1

Linked notes

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