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

HRID 2225499Notes

Reaction equation

HRID 2225499 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][C:8]([CH3:15])([C:11]([O:13]C)=[O:12])[CH2:7][CH2:6]1.Cl>CO>[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][C:8]([CH3:15])([C:11]([OH:13])=[O:12])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19004700Methyl 4-hydroxymethyl-1-methyl-1-cyclohexanecarboxylate

Product 1

HCID 190047944-Hydroxymethyl-1-methyl-1-cyclohexanecarboxylic acidYield 60.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

50 ml of 3N aqueous sodium hydroxide solution was added to a solution of 4.5 g of methyl 4-hydroxymethyl-1-methyl-1-cyclohexanecarboxylate (Example 42) in 100 ml of methanol. The solution was reacted for 2 hours, while it was refluxed. After reaction, 2N hydrochloric acid was added to the reaction 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 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=1:1, the solvent was removed in vacuo, yielding 2.5 g of 4-hydroxymethyl-1-methyl-1-cyclohexanecarboxylic acid as a pale yellow oily, which had the following physiochemical properties:

Workup

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

Sources & evidence

ORD record
ord-141228f0cbc343b0888c36b8da1cda70
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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