2-Hydroxy-4-methoxybenzophenone → 2-(Cyclohexylhydroxymethyl)-5-methoxy-cyclohexanol

HRID 709378Notes

Reaction equation

HRID 709378 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[3H][3H]>C(OCC)(=O)C.[OH-].[Na+].[Rh]>[CH:12]1([CH:10]([OH:11])[CH:3]2[CH2:4][CH2:5][CH:6]([O:8][CH3:9])[CH2:7][CH:2]2[OH:1])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 2

HCID 46322-Hydroxy-4-methoxybenzophenoneHCID 24824Tritium

Product 1

HCID 722012492-(Cyclohexylhydroxymethyl)-5-methoxy-cyclohexanolYield 73.5%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

10 g of (2-hydroxy-4-methoxyphenyl)phenylmethanone (Eusolex® 4360, Merck) are dissolved in 5550 ml of ethyl acetate containing 1 g of 1N NaOH. 10 g of 5% Rh/C catalyst (50% of water) are subsequently added. The hydrogenation is carried out using hydrogen 3.0 at 40° C. and a pressure of 5 bar. When the hydrogenation is complete, the catalyst is separated off by filtration. The solution obtained is transferred into the separating funnel, and the phases are separated. The aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water, subsequently dried over sodium sulfate, filtered and evaporated in a rotary evaporator, giving 7.8 g of product as white solid (cis and trans isomer mixture).

Workup

  1. customat 40° C.
  2. customthe catalyst is separated off by filtration
  3. customThe solution obtained
  4. customthe phases are separated
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. washThe combined organic phases are washed with water
  7. dry with materialsubsequently dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-285ad530cdd14551831398ba2048aafe
Source dataset
uspto-grants-2015_11
Patent number
US09181161B2

Reaction notes

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