Methyl 4-acetyl-1-methyl-3-cyclohexene-1-carboxylate → Methyl 4-acetyl-1-methylcyclohexanecarboxylate

HRID 2225492Notes

Reaction equation

HRID 2225492 reaction equation
[C:1]([C:4]1[CH2:9][CH2:8][C:7]([CH3:14])([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH:5]=1)(=[O:3])[CH3:2].[H][H]>C(O)C.[C].[Pd]>[C:1]([CH:4]1[CH2:9][CH2:8][C:7]([CH3:14])([C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 19004723Methyl 4-acetyl-1-methyl-3-cyclohexene-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 19004752Methyl 4-acetyl-1-methylcyclohexanecarboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

0.1 g of 10% palladium-carbon was added to a solution of 2.1 g of methyl 4-acetyl-1-methyl-3-cyclohexene-1-carboxylate (Example 34) in 50 ml of ethanol. The solution was reacted for 18 hours under normal-pressure hydrogen gas. After reaction, the catalyst was filtered out, and the solvent was removed in vacuo from the filtrate. The oily substance obtained was refined by vacuum distillation (Kugelrohl), yielding 2.1 g of methyl 4-acetyl-1-methyl-1-cyclohexanecarboxylate as a colorless oil, which had the following physiochemical properties:

Workup

  1. customAfter reaction
  2. filtrationthe catalyst was filtered out
  3. customthe solvent was removed in vacuo from the filtrate
  4. customThe oily substance obtained
  5. distillationwas refined by vacuum distillation (Kugelrohl)

Sources & evidence

ORD record
ord-1077847621d24b6c9b9a81b74fdd58a2
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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