HCID 3735677, compound → HCID 69539742, compound

HRID 1737173Notes

Reaction equation

HRID 1737173 reaction equation
[CH2:1]([C:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[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][CH2:11][C@H:10]([OH:14])[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][CH2:11][C@H:10]([OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 3735677HCID 3735677, compound

Product 2

HCID 67578464HCID 67578464, compoundHCID 69539742HCID 69539742, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Then, 9.6 g of 3-benzylcyclohexenone 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 4.5 g of cis-3-benzylcyclohexanol and 4.5 g of trans-3-benzylcyclohexanol (yield: 92% 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-ea1efaf641bf4e29beba64ad181f2807
Source dataset
uspto-grants-1999_10
Patent number
US05962403

Reaction notes

Loading…