3-(Trifluoromethyl)phenol → 1-{4-[3-(Trifluoromethyl)phenoxy]phenyl}ethan-1-one

HRID 1863286Notes

Reaction equation

HRID 1863286 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[CH:4]=1.F[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 73763-(Trifluoromethyl)phenolHCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 31374Dimethylacetamide

Product 1

HCID 125318311-{4-[3-(Trifluoromethyl)phenoxy]phenyl}ethan-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 32.4 g of α,α,α-trifluoro-m-cresol, 27.62 g of p-fluoroacetophenone, 55.2 g of potassium carbonate and 250 ml of N,N-dimethylacetamide is heated under Argon overnight with vigorous stirring at 150°-155° C. After cooling the mixture is added to 500 ml of water and extracted with benzene. The combined extracts are washed with two 100 ml portions of 5% NaOH, 100 ml of H2O, 100 ml of saturated brine, and dried over MgSO4. Evaporation of the solvent at reduced pressure affords a brown liquid which is distilled to give the product as a pale yellow oil (bp 122°-142° C. @ 0.2 mm).

Workup

  1. temperatureis heated under Argon overnight
  2. temperatureAfter cooling the mixture
  3. extractionextracted with benzene
  4. washThe combined extracts are washed with two 100 ml portions of 5% NaOH, 100 ml of H2O, 100 ml of saturated brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent at reduced pressure
  7. customaffords a brown liquid which
  8. distillationis distilled

Sources & evidence

ORD record
ord-a0e749ece3184a6cac493d9714a0f116
Source dataset
uspto-grants-1979_09
Patent number
US04168385

Reaction notes

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