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

HRID 1093490Notes

Reaction equation

HRID 1093490 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([OH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.F[C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=1[C:25]([F:28])([F:27])[F:26].Cl>CN(C)C=O>[CH2:7]([O:14][C:16]1[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]=1[C:25]([F:26])([F:28])[F:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 5222684-Fluoro-3-(trifluoromethyl)benzoic acidHCID 23665647Potassium tert-butoxide

Product 1

HCID 167490234-(Benzyloxy)-3-(trifluoromethyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a solution of potassium t-butoxide (27.5 g) in N,N-dimethylformamide (120 ml) was added dropwise a solution of benzyl alcohol (15.9 ml) in N,N-dimethylformamide (60 ml) over min. The mixture was stirred for 30 min, and a solution of 4-fluoro-3-trifluoromethylbenzoic acid (20.0 g) in N,N-dimethylformamide (90 ml) was added under ice-cooling. The mixture was stirred at room temperature for 1 hr, and further at 50° C. for 1 hr. The reaction mixture was added to ice water, and acidified with 1M hydrochloric acid (300 ml). The precipitated solid was collected by filtration, and washed with water and then hexane to give the object product (28.2 g) as a white powder.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1 hr
  3. waitfurther at 50° C. for 1 hr
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-d17a7f01b4804136b4d732fa17f78b88
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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