Benzaldehyde → (S)-alpha-(Trifluoromethyl)benzyl alcohol
Reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:9][C:10]([Si](C)(C)C)([F:12])[F:11].O>CCCCCC>[C:2]1([CH:1]([OH:8])[C:10]([F:12])([F:11])[F:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
Benzaldehyde was reacted with trifluoromethyltrimethylsilane as in Example 10. After a reaction time of 5 hours, 20 ml of water were added, and the reaction mixture was heated briefly to 80° C. 50 ml of hexane were then added. The reaction mixture was then extracted twice with 100 ml of water, and the resultant organic phase was dried over Na2SO4. On distillation of the crude product, 15.4 g (88% yield) of 1-phenyl-2,2,2-trifluoroethanol (boiling point 68°-69° C./6 mbar) were obtained.
Workup
- extractionThe reaction mixture was then extracted twice with 100 ml of water
- dry with materialthe resultant organic phase was dried over Na2SO4
- distillationOn distillation of the crude product
Sources & evidence
- ORD record
- ord-15bdb696565d45b18391453cc4922b27
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04968848
Reaction notes
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