Reaction #1744

Reaction equation

4-phenylcyclohexanone

sodium borohydride

→

4-phenylcyclohexanol

Yield 66.2%

Solvents

methanol

Conditions

Workup

1. 1
   Otherto react for 0.5 hours at -10° C. and for 3 hours at ambient temperature
2. 2
   Otherevaporated down in vacuo
3. 3
   workup.ADDITIONThe residue remaining is mixed with water
4. 4
   OtherThe suspension formed
5. 5
   workup.STIRRINGis stirred for 1 hour
6. 6
   Filtrationfiltered
7. 7
   Otherdried
8. 8
   Otherrecrystallised from diisopropylether

Procedure

To a solution of 31.4 g (0.18 mol) of 4-phenylcyclohexanone in 500 ml of absolute methanol, which is cooled to -10° C., are added 6.8 g (0.18 mol) of sodium borohydride in batches with stirring. The reaction mixture is allowed to react for 0.5 hours at -10° C. and for 3 hours at ambient temperature and then evaporated down in vacuo. The residue remaining is mixed with water and acidified with 2N hydrochloric acid. The suspension formed is stirred for 1 hour and the crystalline product is suction filtered, dried and recrystallised from diisopropylether. 21 g (66% of theory) of 4-phenylcyclohexanol are obtained, melting point: 112°-114° C.

Source