Hydrochloric Acid → 1-Methyl-4-oxocyclohexane-1-carboxylic acid

HRID 2225486Notes

Reaction equation

HRID 2225486 reaction equation
[OH-].[Na+].[CH3:3][C:4]1([C:11]([O:13]C)=[O:12])[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1.Cl>CO>[CH3:3][C:4]1([C:11]([OH:13])=[O:12])[CH2:5][CH2:6][C:7](=[O:10])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12568255Methyl 1-methyl-4-oxocyclohexane-1-carboxylate

Product 1

HCID 226099431-Methyl-4-oxocyclohexane-1-carboxylic acidYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 ml of a 3N aqueous sodium hydroxide solution was added to a solution of 5 g of methyl 1-methyl-4-oxo-1-cyclohexanecarboxylate, which is disclosed in a literature [T. Sohda, K. Meguro, and Y. Kawamatsu, Chem. Pharm. Bull., 32, 2267-2278 (1984)], in 150 ml of methanol. The resultant solution was reacted for 2 hours, while it was refluxed. After reaction, 2N hydrochloric acid was added to the solution, acidifying the solution. The solution was extracted five times with 50 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution and was then dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 50 g of silica gel. From the fraction eluted with hexane and ethyl acetate=2:1, the solvent was removed in vacuo, yielding 4.1 g of 1-methyl-4-oxo-1-cyclohexanecarboxyic acid as a colorless oil, which had the following physiochemical properties:

Workup

  1. temperaturewas refluxed
  2. additionwas added to the solution
  3. extractionThe solution was extracted five times with 50 ml of ethyl acetate
  4. customThe organic layer obtained
  5. washwas washed three times with an aqueous sodium chloride solution
  6. dry with materialwas then dried over magnesium sulfate
  7. customThereafter, the solvent was removed in vacuo
  8. customThe oily substance obtained
  9. washFrom the fraction eluted with hexane and ethyl acetate=2:1
  10. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d8796d02f91a4fa0a02ffefcb589aac1
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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