Ammonium Chloride → 1-(4-Fluorophenyl)-1-(4-benzyloxyphenyl)-propan-1-ol

HRID 364773Notes

Reaction equation

[CH2:1]([Li])[CH3:2].[F:4][C:5]1[CH:26]=[CH:25][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)=[O:10])=[CH:7][CH:6]=1.[Cl-].[NH4+]>CCOCC>[F:4][C:5]1[CH:26]=[CH:25][C:8]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)([OH:10])[CH2:1][CH3:2])=[CH:7][CH:6]=1

Participants

Conditions

Temperature: -20 °C

Procedure

To 125 ml. of a 0.8 molar ethereal ethyl lithium solution a solution of 12.25 g. of 4-fluoro-4'-benzyloxy-benzophenone in 180 ml. of dry ether is added dropwise, in argon atmosphere, with stirring at -20° C. The reaction mixture is allowed to warm up to room temperature and stirred for further 90 minutes. It is then poured into saturated aqueous ammonium chloride solution under cooling. The aqueous phase is extracted with ether, the organic phases are combined and washed to neutral with water. After drying over anhydrous magnesium sulfate ether is distilled off under reduced pressure. The solid residue is crystallized from a mixture of ethyl acetate and n-heptane to yield 7.4 g. of the named compound, melting at 56°-57° C.

Workup

temperatureto warm up to room temperature
stirringstirred for further 90 minutes
temperatureunder cooling
extractionThe aqueous phase is extracted with ether
washwashed to neutral with water
dry with materialAfter drying over anhydrous magnesium sulfate ether
distillationis distilled off under reduced pressure
customThe solid residue is crystallized from a mixture of ethyl acetate and n-heptane
customto yield 7.4 g

Sources & evidence

ORD record: ord-7da82f9233394934af5031081598d31a
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04605785

Reaction notes

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