Methyl 1-methyl-4-oxocyclohex-2-ene-1-carboxylate → Methyl 1-methyl-4-oxocyclohexane-1-carboxylate

HRID 1462920Notes

Reaction equation

HRID 1462920 reaction equation
[CH3:1][C:2]1([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:6][C:5](=[O:8])[CH:4]=[CH:3]1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][C:2]1([C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:4][C:5](=[O:8])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 12563054Methyl 1-methyl-4-oxocyclohex-2-ene-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 12568255Methyl 1-methyl-4-oxocyclohexane-1-carboxylateYield 95.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 1-methyl-4-oxo-2-cyclohexenecarboxylate [J. Am. Chem. Soc., 101, 6996 (1979)] (100 g) was dissolved in ethyl acetate (600 ml), 10% Pd-C (5 g) was added, and catalytic reduction was carried out at room temperature and 1 atomosphere. About 14 liters of hydrogen was absorged in about 2 hours. The catalyst was filtered off, and the filtrate was concentrated and distilled under reduced pressure to give methyl 1-methyl-4-oxocyclohexanecarboxylate (96.5 g, 95.4%, b.p. 82°-84° C./0.5 mmHg).

Workup

  1. customwas carried out at room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c77248bc3b11478daaea9479e8f9fd07
Source dataset
uspto-grants-1984_07
Patent number
US04461902

Reaction notes

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