1-(4-Cyclohexylphenyl)ethan-1-one → 1-(4-Cyclohexylphenyl)ethanol

HRID 461508Notes

Reaction equation

HRID 461508 reaction equation
[BH4-].[Na+].[CH:3]1([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>CO>[CH:3]1([C:9]2[CH:10]=[CH:11][C:12]([CH:15]([OH:17])[CH3:16])=[CH:13][CH:14]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 877151-(4-Cyclohexylphenyl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 126314581-(4-Cyclohexylphenyl)ethanolYield 102.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

11.4 gm (0.3 mol) of sodium borohydride were added in small portions at 20°-25° C to 60.7 gm (0.3 mol) of 4'-cyclohexyl-acetophenone (m.p. 66°-67° C) in 300 ml of methanol while stirring vigorously and cooling on ice. The resulting mixture was then stirred for another hour at room temperature, and the reaction product was precipitated with acidified ice water. After suction filtering, washing and drying, 62.6 gm of crystalline material were obtained. A sample, recrystallized from petroleum ether, melted at 81.5°-82.5° C.

Workup

  1. temperaturecooling on ice
  2. stirringThe resulting mixture was then stirred for another hour at room temperature
  3. customthe reaction product was precipitated with acidified ice water
  4. filtrationAfter suction filtering
  5. washwashing
  6. customdrying

Sources & evidence

ORD record
ord-c3d44be31e404ec98f7e73efc7b2fbb6
Source dataset
uspto-grants-1977_12
Patent number
US04062973

Reaction notes

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