Hydrochloric Acid → 4-(cis-4-Hydroxycyclohexyl)phenol

HRID 2220002Notes

Reaction equation

HRID 2220002 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[OH:14][CH:11]1[CH2:10][CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 45989164-(4'-Hydroxyphenyl)cyclohexanone

Product 1

HCID 101764984-(cis-4-Hydroxycyclohexyl)phenolYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 g (0.052 mol) of 4-(4-Hydroxy-phenyl)-cyclohexanone is dissolved in 300 mL of methanol. 2.13 g (0.058 mol) of NaBH4 is added at room temperature by small portion for 2 hours. After stirring over night, the mixture is cooled using an ice-water bath, then hydrolysed with a solution of 10% HCl aqueous solution. The solution is extracted several times with ethyl acetate. The resulting organic phase is washed with water, dried over magnesium sulfate, then concentrated under reduced pressure. The residue recrystallised from ethanol gives pure white crystals (8.7 g, 87% yield).

Workup

  1. temperaturethe mixture is cooled
  2. extractionThe solution is extracted several times with ethyl acetate
  3. washThe resulting organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue recrystallised from ethanol

Sources & evidence

ORD record
ord-d92ced5a02524aa68a92a454c1c763b7
Source dataset
uspto-grants-2008_08
Patent number
US07416682B2

Reaction notes

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