Sulfuric Acid → Methyl 4-hydroxycyclohexanecarboxylate

HRID 1873561Notes

Reaction equation

HRID 1873561 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.S(=O)(=O)(O)O.[C:16](OCC)(=O)C.C(=O)(O)[O-].[Na+]>CO>[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:16])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 1511384-Hydroxycyclohexanecarboxylic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 87117Methyl 4-hydroxycyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.00 g (34.68 mmol) of 4-hydroxycyclohexanecarboxylic acid are dissolved in 80 ml of methanol, and 2 ml of conc. sulfuric acid are added slowly. The mixture is stirred under reflux for 20 h. After cooling to RT, the mixture is carefully poured into a mixture of 100 ml of ethyl acetate and 100 ml of saturated aqueous sodium bicarbonate solution. The phases are separated, and the organic phase is washed once with 20 ml of saturated aqueous ammonium chloride solution. The organic phase is dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The crude product is directly used in the next reaction without further purification.

Workup

  1. temperatureunder reflux for 20 h
  2. customThe phases are separated
  3. washthe organic phase is washed once with 20 ml of saturated aqueous ammonium chloride solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvent is removed on a rotary evaporator
  6. customThe crude product is directly used in the next reaction without further purification

Sources & evidence

ORD record
ord-236b08fc89484a3f82198f42e877d502
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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