Reaction #2199

Reaction equation

4-chloro-4'-trifluoromethylsulfonylmethylbenzophenone

Sodium borohydride

→

desired product

Yield 77.0%

4-Chloro-4'-trifluoromethylsulfonylmethylbenzhydrol

Yield 77.0%

Solvents

methanol

methanol

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was further stirred overnight at room temperature
2. 2
   workup.DISTILLATIONwas distilled off under reduced pressure
3. 3
   ExtractionThe residue was extracted with ethyl acetate (250 ml)
4. 4
   WashThe extract was washed with water
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONThen, ethyl acetate was distilled off under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Procedure

4-chloro-4'-trifluoromethylsulfonylmethylbenzophenone (5.5 g) was dispersed in methanol (200 ml). Sodium borohydride was gradually added thereto at room temperature with stirring, and the mixture was further stirred overnight at room temperature. After completion of the reaction, methanol was distilled off under reduced pressure. The residue was extracted with ethyl acetate (250 ml). The extract was washed with water and dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the desired product as a white powder (4.2 g, melting point: 113° to 115° C., yield: 77%).

Source