Sulfuric Acid → Methyl 4-methoxycyclohexane-1-carboxylate

HRID 56894

Reaction equation

HRID 56894 reaction equation
S(=O)(=O)(O)O.[CH3:6][O:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1.[C:17](=O)(O)[O-].[Na+]>CO>[CH3:6][O:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 736153Rac-(1r,4r)-4-methoxycyclohexane-1-carboxylic acid

Product 1

HCID 53849879Methyl 4-methoxycyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.8 ml of concentrated sulphuric acid were added to a solution of 4.00 g (25.3 mmol) of 4-methoxycyclohexanecarboxylic acid in 32 ml of methanol, and the resulting reaction solution was heated under reflux overnight. The mixture was cooled to room temperature and the pH was adjusted to 7-8 using saturated aqueous sodium bicarbonate solution. The mixture was then extracted three times with 70 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate and filtered, and the solvent was removed under reduced pressure. The crude product corresponded to the title compound. Yield: 4.30 g (99% of theory)

Workup

  1. customthe resulting reaction solution
  2. temperaturewas heated
  3. temperatureunder reflux overnight
  4. extractionThe mixture was then extracted three times with 70 ml of ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-10af66dab0b346579972b559ef70da67
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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