Benzyl Alcohol → 3-(Benzyloxy)-4-(trifluoromethyl)benzoic acid

HRID 1755112Notes

Reaction equation

HRID 1755112 reaction equation
CC(C)([O-])C.[K+].F[C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[C:11]([OH:13])=[O:12].[CH2:21]([OH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Cl>CS(C)=O>[CH2:21]([O:28][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[C:11]([OH:13])=[O:12])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 6882933-Fluoro-4-(trifluoromethyl)benzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 167478443-(Benzyloxy)-4-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium tert-butoxide (816 mg, 7.28 mmol) was added to a solution of 3-fluoro-4-trifluoromethyl-benzoic acid (682 mg, 3.28 mmol) and benzyl alcohol (471 mg, 4.36 mmol) in DMSO (7.3 ml), and the mixture was stirred at room temperature for 16 hours. The reaction solution was made acidic by adding concentrated hydrochloric acid, and the precipitated insoluble matter was then filtered off. The resulting solid was washed with water and then dried to give 3-benzyloxy-4-trifluoromethyl-benzoic acid as a crude compound.

Workup

  1. filtrationthe precipitated insoluble matter was then filtered off
  2. washThe resulting solid was washed with water
  3. customdried

Sources & evidence

ORD record
ord-a639086764e34d4cbe06ae5c9e3108ea
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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