Water → 4-(Benzyloxy)-3-(trifluoromethyl)benzaldehyde

HRID 28834Notes

Reaction equation

HRID 28834 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:14]([O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]([F:11])([F:12])[F:13])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 70215934-Hydroxy-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 184436844-(Benzyloxy)-3-(trifluoromethyl)benzaldehydeYield 75.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxy-3-(trifluoromethyl)benzaldehyde (1.5 g, 8.0 mmol), benzyl bromide (1.51 g, 8.8 mmol) and potassium carbonate (1.66 g, 12.0 mmol) in dimethyl formamide (20 mL) was stirred water (100 mL) and extracted 3 times with ethyl acetate. The ethyl acetate extracts were combined and washed 2 times with water and dried over magnesium sulfate. Concentration in vacuo yielded 1.7 g of 4-benzyloxy-3-trifluoromethyl-benzaldehyde which was used as such in the next step.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. washwashed 2 times with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-8f79f436035a41d19ee97a7dfbbbaa65
Source dataset
uspto-grants-2008_09
Patent number
US07419980B2

Reaction notes

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