Benzyl Alcohol → 4-Benzyloxy-2-(trifluoromethyl)benzoic acid

HRID 350626Notes

Reaction equation

HRID 350626 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.F[C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([C:21]([F:24])([F:23])[F:22])[CH:13]=1.Cl>CN(C=O)C>[CH2:3]([O:10][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([C:21]([F:22])([F:24])[F:23])[CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 6882554-Fluoro-2-(trifluoromethyl)benzoic acid

Product 1

HCID 190139184-Benzyloxy-2-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 5.2 g portion of 60% sodium hydride oil dispersion was suspended in 50 ml of DMF, and 6.73 ml of benzyl alcohol was added thereto under ice-cooling. After warming up to room temperature, 12.3 g of 4-fluoro-2-trifluoromethylbenzoic acid was added thereto and stirred at room temperature for 6 hours. A 1 M hydrochloric acid aqueous solution was added to the reaction mixture, and the thus precipitated crystals were collected by filtration to obtain 16.39 g of 4-(benzyloxy)-2-(trifluoromethyl)benzoic acid.

Workup

  1. temperatureunder ice-cooling
  2. filtrationthe thus precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-d569174154e64f60a78bf22b698acdc1
Source dataset
uspto-grants-2007_02
Patent number
US07183271B2

Reaction notes

Loading…