Water → 5,5,5-Trifluoro-3-methyl-2-(4-methylphenyl)pentanoic acid
Reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[F:22][C:23]([F:38])([F:37])[CH2:24][CH:25]([CH3:36])[CH:26]([C:29]1[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=1)[CH2:27][OH:28].[OH2:39]>CN(C=O)C>[F:22][C:23]([F:37])([F:38])[CH2:24][CH:25]([CH3:36])[CH:26]([C:29]1[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=1)[C:27]([OH:39])=[O:28]Participants
Procedure
26.7 g (71.1 mmol) of pyridinium dichromate were added to 5 g (20.3 mmol) of 5,5,5-trifluoro-3-methyl-2-(4-methylphenyl)pentan-1-ol in 83 ml of DMF, and the mixture was stirred at room temperature for 12 hours. The reaction mixture was subsequently added to 100 ml of water, the organic phase was separated off and the aqueous phase was extracted six more times with diethyl ether. The combined organic phases were extracted five times with 0.5 M aqueous sodium hydroxide solution. The combined aqueous-basic phases were then acidified to about pH 3 with 3 M hydrochloric acid and extracted six times with ethyl acetate. The combined ethyl acetate phases were dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. This gave 3.79 g (14.56 mmol, 71% of theory) of the title compound as a colorless oil.
Workup
- customthe organic phase was separated off
- extractionthe aqueous phase was extracted six more times with diethyl ether
- extractionThe combined organic phases were extracted five times with 0.5 M aqueous sodium hydroxide solution
- extractionextracted six times with ethyl acetate
- dry with materialThe combined ethyl acetate phases were dried over magnesium sulfate
- filtrationfiltered
- customthe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-f1e01aa46e724d7f93ac920b0d40435b
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987256B2
Reaction notes
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