4-benzyl-2-cyclohexen-1-one → HCID 178521556, compound

HRID 1737171Notes

Reaction equation

HRID 1737171 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]=[CH:9]1)[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][C@H:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 117692464-benzyl-2-cyclohexen-1-one

Product 2

HCID 178521555HCID 178521555, compoundHCID 178521556HCID 178521556, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Besides, 30 g of the above-obtained 4-benzyl-2-cyclohexen-1-one were hydrogenated at room temperature for 6 hours using 5 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 13 g of cis-4-benzylcyclo-hexanol and 14 g of trans-4-benzylcyclohexanol (yield: 90% in total).

Workup

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

Sources & evidence

ORD record
ord-492ed2414c714ced9ae98803b82a15f4
Source dataset
uspto-grants-1999_10
Patent number
US05962403

Reaction notes

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