4-Hydroxybenzophenone → 4-(Cyclohexylhydroxymethyl)cyclohexanol

HRID 709379Notes

Reaction equation

HRID 709379 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:4][CH:3]=1.[3H][3H]>C(OCC)(=O)C.[Rh]>[CH:10]1([CH:8]([OH:9])[CH:5]2[CH2:4][CH2:3][CH:2]([OH:1])[CH2:7][CH2:6]2)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 143474-HydroxybenzophenoneHCID 24824Tritium

Product 1

HCID 722012454-(Cyclohexylhydroxymethyl)cyclohexanolYield 84%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1 g of (4-hydroxyphenyl)phenylmethanone are dissolved in 50 ml of ethyl acetate. 1 g of 5% Rh/C catalyst (50% of water) is subsequently added. The hydrogenation is carried out using hydrogen 3.0 at 40° C. and a pressure of 2 bar. When the hydrogenation is complete, the catalyst is separated off by filtration, and the solution is evaporated in a rotary evaporator, giving 900 mg of product (cis and trans isomer mixture).

Workup

  1. customat 40° C.
  2. customthe catalyst is separated off by filtration
  3. customthe solution is evaporated in a rotary evaporator

Sources & evidence

ORD record
ord-4f0c9e2a46034c49ae96b8bf7b74388e
Source dataset
uspto-grants-2015_11
Patent number
US09181161B2

Reaction notes

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