(4-Prop-1-en-2-ylcyclohexen-1-yl)methanol → [4-(Propan-2-yl)cyclohexyl]methanol

HRID 1730610Notes

Reaction equation

HRID 1730610 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][C:7]([CH2:10][OH:11])=[CH:6][CH2:5]1)([CH3:3])=[CH2:2]>C(O)C.[Ni]>[CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 10819(4-Prop-1-en-2-ylcyclohexen-1-yl)methanol

Product 1

HCID 83763[4-(Propan-2-yl)cyclohexyl]methanol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

10 g of 4-isopropenyl-cyclohex-1-enylmethanol dissolved in 200 ml of ethanol were hydrogenated at atmospheric pressure in the presence of 200 mg of Raney nickel. The reaction mixture was then filtered, evaporated and finally subjected to a fractional distillation. It was thus isolated a product having bp 75° - 115°/10 Torr. The vapour phase chromatography analysis showed that the isolated product contained 50% of a 60 : 40 (parts by weight) mixture of cis and trans isomers of the desired alcohol.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customevaporated
  3. distillationfinally subjected to a fractional distillation
  4. customIt was thus isolated a product

Sources & evidence

ORD record
ord-c95d78e86b2242ffb298fb7752c52229
Source dataset
uspto-grants-1976_11
Patent number
US03993604

Reaction notes

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