Hydrochloric Acid → Benzenepropanol,3-phenoxy-

HRID 414291Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][C:22](OC)=[O:23])[CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.Cl>O1CCCC1.[Cl-].[Na+]>[O:7]([C:14]1[CH:15]=[C:16]([CH2:20][CH2:21][CH2:22][OH:23])[CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

temperatureto warm up to the ambient temperature (ca. 22° C.)
extractionextracted with diethyl ether (×4) and with ethyl acetate
dry with materialThe combined extracts were dried over anhydrous sodium sulphate
concentrationconcentrated by evaporation of the solvent under reduced pressure

Sources & evidence

ORD record: ord-11202ba2dd5c46128b8983de336c2492
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04791139

Reaction notes

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