Methanol → Methyl 2-hydroxy-3-isopropylbenzoate

HRID 1642645Notes

Reaction equation

HRID 1642645 reaction equation
[OH:1][C:2]1[C:10]([CH:11]([CH3:13])[CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14]O>S(=O)(=O)(O)O>[CH3:14][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:2]=1[OH:1]

Participants

4

Reactant 2

HCID 887MethanolHCID 2018873-Isopropylsalicylic acid

Product 1

HCID 18469877Methyl 2-hydroxy-3-isopropylbenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst2×

Conditions

Temperature
45 °C

Procedure

To a solution of 2-hydroxy-3-isopropylbenzoic acid (4.5 g, 25 mmol) in MeOH (75 mL) is added 10 drops of sulfuric acid and the mixture is heated in an oil bath at 45° C. for 18 h. Extra sulfuric acid (10 drops) is added and the mixture is heated again at 60° C. for 18 h. Solvent is evaporated under reduced pressure and the residue is dissolved in EtOAc. The organic phase is then washed with saturated NaHCO3 (4×), water (1×) and brine and is dried with Na2SO4 and MgSO4, and concentrated. The residue is purified by flash column chromatography to give the title compound as an oil.

Workup

  1. temperaturethe mixture is heated again at 60° C. for 18 h
  2. customSolvent is evaporated under reduced pressure
  3. dissolutionthe residue is dissolved in EtOAc
  4. washThe organic phase is then washed with saturated NaHCO3 (4×), water (1×) and brine
  5. dry with materialis dried with Na2SO4 and MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-0576ffe6ad874711a2c8e3173a8dd6ce
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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