Ethanone, 1-(3-phenoxyphenyl)- → 1-(3-Phenoxyphenyl)ethanol

HRID 1759415Notes

Reaction equation

HRID 1759415 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([C:14](=[O:16])[CH3:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]([OH:16])[CH3:15])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 36249Ethanone, 1-(3-phenoxyphenyl)-HCID 4311764Sodium borohydride

Product 1

HCID 128824191-(3-Phenoxyphenyl)ethanol

Procedure

m-Phenoxyacetophenone is reduced with sodium borohydride to form alpha-(m-phenoxyphenyl)ethyl alcohol which is then reacted with phosphorus tribromide to form alpha-(m-phenoxyphenyl)ethyl bromide. This product is reacted with sodium cyanide under heat in dimethyl sulfoxide. Hydrolysis of the product with sodium hydroxide gives the desired alpha-(m-phenoxyphenyl)propionic acid. (For details, see U.S. Pat. No. 3,600,437).

Sources & evidence

ORD record
ord-5bf6ec19a67c4957ab80a2777e68908a
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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