Hydrochloric Acid → 4-Acetyl-1-methyl-1-cyclohexanecarboxylic acid

HRID 2225493Notes

Reaction equation

HRID 2225493 reaction equation
[OH-].[Na+].[C:3]([CH:6]1[CH2:11][CH2:10][C:9]([CH3:16])([C:12]([O:14]C)=[O:13])[CH2:8][CH2:7]1)(=[O:5])[CH3:4].Cl>C(O)C>[C:3]([CH:6]1[CH2:11][CH2:10][C:9]([CH3:16])([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19004752Methyl 4-acetyl-1-methylcyclohexanecarboxylate

Product 1

HCID 190047484-Acetyl-1-methyl-1-cyclohexanecarboxylic acidYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 ml of a 2N aqueous sodium hydroxide solution was added to a solution of 2.1 g of methyl 4-acetyl-1-methyl-1-cyclohexanecarboxylate (Example 35) in 20 ml of ethanol. The solution was reacted for 4 hours, while it was refluxed. After reaction, 2N hydrochloric acid was added to the reaction solution, acidifying the solution. The solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed twice with an aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo, and the product obtained was recrystallized from ethyl acetate/hexane, yielding 1.4 g of 4-acetyl-1-methyl-1-cyclohexanecarboxylic acid as white crystal, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 4 hours, while it
  2. temperaturewas refluxed
  3. additionwas added to the reaction solution
  4. extractionThe solution was extracted three times with 50 ml of ethyl acetate
  5. customThe organic layer obtained
  6. washwas washed twice with an aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed in vacuo
  9. customthe product obtained
  10. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a441732bd8e846fb9287cd1747be1916
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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