4-Phenylcyclohexanone → 4-Phenylcyclohexanol

HRID 1648

Reaction equation

HRID 1648 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO>[C:1]1([CH:7]2[CH2:8][CH2:9][CH:10]([OH:13])[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 786054-PhenylcyclohexanoneHCID 4311764Sodium borohydride

Product 1

HCID 794974-PhenylcyclohexanolYield 66.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. customto react for 0.5 hours at -10° C. and for 3 hours at ambient temperature
  2. customevaporated down in vacuo
  3. additionThe residue remaining is mixed with water
  4. customThe suspension formed
  5. stirringis stirred for 1 hour
  6. filtrationfiltered
  7. customdried
  8. customrecrystallised from diisopropylether

Sources & evidence

ORD record
ord-59ad5f10a39944bab640d9fbd6671548
Source dataset
uspto-grants-1998_03
Patent number
US05726205

Linked notes

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