Hydrochloric Acid → Benzenepropanol,3-phenoxy-

Participants

Reaction Conditions

Reaction Steps

Lithium aluminium hydride (60 cm3 of a 1M solution in tetrahydrofuran) was added dropwise over a period of 10 minutes to a stirred solution of methyl 3-(3-phenoxyphenyl)propanoate (25.6 g) in tetrahydrofuran (30 cm3) whilst the temperature was maintained at 0° C. by external cooling. Stirring was continued for a further 45 minutes after which the mixture was allowed to warm up to the ambient temperature (ca. 22° C.). Iced water was added carefully to the mixture which was then acidified with dilute hydrochloric acid at pH2. The mixture was diluted with saturated sodium chloride solution and extracted with diethyl ether (×4) and with ethyl acetate. The combined extracts were dried over anhydrous sodium sulphate and concentrated by evaporation of the solvent under reduced pressure to yield 3-(3-phenoxyphenyl)propan-1-ol (22 g, 100% by gas-liquid chromatography) as a colourless oil.

Provenance & Evidence