2-Benzylidenecyclohexanone → HCID 12118799, compound

HRID 1737175Notes

Reaction equation

HRID 1737175 reaction equation
[CH:1](=[C:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Ni].CO>[CH2:1]([C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 989262-Benzylidenecyclohexanone

Product 2

HCID 12118799HCID 12118799, compoundYield 88%HCID 12283992Cyclohexanol, 2-(phenylmethyl)-, cis-

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Then, 10 g of 2-benzylidenecyclohexanone were hydrogenated at room temperature using 1 g of Raney nickel in methanol under hydrogen pressure (3 kg/cm2) until the absorption of hydrogen was stopped. After an organic layer was collected by decantation and concentrated, the residue was purified by column chromatography, thereby obtaining 4.6 g of cis-2-benzylcyclohexanol and 4.4 g of trans-2-benzylcyclohexanol (yield: 88% in total).

Workup

  1. customwere hydrogenated at room temperature
  2. customuntil the absorption of hydrogen
  3. customAfter an organic layer was collected by decantation
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-66b69874a6dd4b8db91e126567b090d3
Source dataset
uspto-grants-1999_10
Patent number
US05962403

Reaction notes

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