p-METHYLACETOPHENONE → 4,4,4-Trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one

HRID 386747Notes

Reaction equation

HRID 386747 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)=[O:4].[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:26])=[O:25])=[CH:20][CH:19]=1.[H-].[Li+]>O1CCCC1.C(OC)(C)(C)C>[F:1][C:2]([F:15])([F:16])[C:3]([OH:4])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)[CH2:26][C:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:17])=[CH:19][CH:20]=1)=[O:25]

Participants

6

Reactant 3

HCID 8500p-METHYLACETOPHENONEHCID 62714Lithium hydrideHCID 1365592,2,2-Trifluoro-3'-(trifluoromethyl)acetophenone

Product 1

HCID 866433794,4,4-Trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-oneYield 97.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 2,2,2-trifluoro-1-[3-(trifluoromethyl)-phenyl]ethanone (3.0 g), 4-methylacetophenone (1.1 g) and lithium hydride (0.13 g) in tetrahydrofuran (30 mL) was stirred for 3 hours at 60° C. After the reaction solution was diluted with t-butylmethylether, the solution was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was then purified by silica gel chromatography to yield 4,4,4-trifluoro-3-hydroxy-1-(4-methylphenyl)-3-[3-(trifluoromethyl)phenyl]butan-1-one (3.0 g).

Workup

  1. washthe solution was washed with water and saturated brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-96b2ea78106642a58b9b8b44317b6dac
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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