Hydrochloric Acid → 4-Chloro-2-(3-trifluoromethyl-phenoxy)-benzyl alcohol

HRID 437829Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1.[BH4-].[Li+].Cl>O1CCCC1>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=2)[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 103 g. of 4-chloro-2-(3-trifluoromethyl-phenoxy)-benzoic acid methyl ester in 400 ml. of tetrahydrofuran is added dropwise at reflux over a period of 30 minutes to a solution of 16.2 g. of lithium borohydride in 280 ml. of absolute tetrahydrofuran. The mixture is then cooled to 0° C. and slowly added dropwise to 400 ml. of 3-N aqueous hydrochloric acid. After the addition of 500 ml. of water, the mixture is extracted twice with ether. After evaporation of the ether, there is obtained 4-chloro-2-(3-trifluoromethyl-phenoxy)-benzyl alcohol in the form of an oil.

Workup

temperatureat reflux over a period of 30 minutes to a solution of 16.2 g
additionslowly added dropwise to 400 ml
additionAfter the addition of 500 ml
extractionof water, the mixture is extracted twice with ether
customAfter evaporation of the ether

Sources & evidence

ORD record: ord-66b91c9763434a928187bf5fcf85df48
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04032525

Reaction notes

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