3,5-Dimethyl-1-(carbethoxymethylene)cyclohexane → Ethyl 3,5-dimethyl-cyclohexylacetate

HRID 1461953Notes

Reaction equation

HRID 1461953 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][C:4](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3]1>[Ni].CO>[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][CH:4]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:3]1

Participants

4

Reactant 1

HCID 146168253,5-Dimethyl-1-(carbethoxymethylene)cyclohexane

Product 1

HCID 20454256Ethyl 3,5-dimethyl-cyclohexylacetateYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a 1 liter autoclave which is fitted with heating means, cooling means and a stirrer are added 54 g of ethyl 3,5-dimethyl-cyclohexylideneacetate, 200 ml of absolute methanol and 3 g of Raney-nickel, which has been washed three times with absolute methanol. The mixture is hydrogenated at 100° C. under a hydrogen pressure of 40 atmospheres. The hydrogen uptake stops after 8 hours. The catalyst is filtered off, the filtrate is concentrated and the residue is distilled. There are obtained 52.3 g of ethyl 3,5-dimethyl-cyclohexylacetate.

Workup

  1. customTo a 1 liter autoclave which is fitted with heating means
  2. temperaturecooling means and a stirrer
  3. washhas been washed three times with absolute methanol
  4. customis hydrogenated at 100° C. under a hydrogen
  5. filtrationThe catalyst is filtered off
  6. concentrationthe filtrate is concentrated
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-4173557b978d467397387dd106b378f0
Source dataset
uspto-grants-1984_07
Patent number
US04457862

Reaction notes

Loading…