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

HRID 1980111Notes

Reaction equation

HRID 1980111 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[CH3:12][C:13]([C:15]1[CH:20]=[CH:19][C:18](F)=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][C:18]1[CH:19]=[CH:20][C:15]([C:13](=[O:14])[CH3:12])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 98284'-FluoroacetophenoneHCID 11430Potassium Carbonate

Product 1

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

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A stirred mixture of 90.6 g of 3-(trifluoromethyl)phenol, 55.2 g of 4-fluoroacetophenone and 400 ml of dry dimethylacetamide was treated under argon with 71.9 g of anhydrous potassium carbonate in portions. The mixture was stirred and refluxed at 155°-160° C. on an oil bath for 18 hours. The mixture was cooled, poured into 1.5 Kg of ice and extracted with three portions of ether. The extracts were combined, washed successively with water, three 100 ml. portions of cold 1N sodium hydroxide, water and then brine, dried and evaporated to an oil. This oil was distilled at 105°-120° C., 0.15-0.20 mm Hg, giving the desired intermediate as an oil, bp 130°-142° C. (0.2 mm).

Workup

  1. temperaturerefluxed at 155°-160° C. on an oil bath for 18 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with three portions of ether
  4. washwashed successively with water, three 100 ml
  5. dry with materialportions of cold 1N sodium hydroxide, water and then brine, dried
  6. customevaporated to an oil
  7. distillationThis oil was distilled at 105°-120° C.

Sources & evidence

ORD record
ord-5f06e004e0aa47329ef3941bdc318cfc
Source dataset
uspto-grants-1984_11
Patent number
US04485114

Reaction notes

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