(4-tert-Butylcyclohexylidene)acetic acid methyl ester → Methyl 2-(4-tert-butylcyclohexyl)acetate

HRID 365648Notes

Reaction equation

HRID 365648 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]=[C:5]1[CH2:10][CH2:9][CH:8]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6]1>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH:5]1[CH2:6][CH2:7][CH:8]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 10750958(4-tert-Butylcyclohexylidene)acetic acid methyl ester

Product 1

HCID 12808867Methyl 2-(4-tert-butylcyclohexyl)acetate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(4-tert-Butylcyclohexylidene)acetic acid methyl ester (10.78 g, 51.3 mmol) was dissolved in methanol (50 ml). Palladium hydroxide on carbon (1.0 g) was added and the reaction mixture was stirred at room temperature under an atmosphere of hydrogen overnight. The catalyst was then removed by filtration through celite and the filtrate was evaporated in vacuo to a clear oil (9.81 g, 91%). 1H-NMR; δ (CDCl3) (as a mixture of cis-trans isomers), 3.67 (3H, s), 2.38 (1H, d, J=8 Hz), 2.18 (1H, d, 7 Hz), 1.85-1.44 (5H, m), 1.20-0.89 (5H, m) and 0.86 (9H, s).

Workup

  1. customThe catalyst was then removed by filtration through celite
  2. customthe filtrate was evaporated in vacuo to a clear oil (9.81 g, 91%)

Sources & evidence

ORD record
ord-9bdc0d6c2a274ffe9190b58f760904f7
Source dataset
uspto-grants-2000_10
Patent number
US06127427

Reaction notes

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