Hydrochloric Acid → 1-(4-Cyclohexylphenyl)ethanol

HRID 917913Notes

Reaction equation

HRID 917913 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.Cl>O.CO>[CH3:16][CH:15]([C:12]1[CH:11]=[CH:10][C:9]([CH:3]2[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)=[CH:14][CH:13]=1)[OH:17]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 877151-(4-Cyclohexylphenyl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 126314581-(4-Cyclohexylphenyl)ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

While cooling well, a solution of 2.5 g of sodium borohydride in 10 ml of water is added dropwise to a solution of 20.2 g of para-cyclohexyl-acetophenone in 250 ml of methanol. The mixture is stirred at room temperature for 1 hour and the pH then adjusted to 2 with semi-concentrated hydrochloric acid. The batch is evaporated completely and the residue extracted several times with ether. The solution is dried and the ether evaporated to obtain methyl-(para-cyclohexylphenyl)-carbinol in the form of colorless crystals melting at 81°-83°C.

Workup

  1. temperatureWhile cooling well
  2. customThe batch is evaporated completely
  3. extractionthe residue extracted several times with ether
  4. customThe solution is dried
  5. customthe ether evaporated

Sources & evidence

ORD record
ord-ad10d98974ae41549853c9502ae9cf5a
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

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