Methanol → Methyl 3-acetyl-2-hydroxybenzoate

HRID 876541Notes

Reaction equation

HRID 876541 reaction equation
[C:1]([C:4]1[C:5]([OH:13])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].OS(O)(=O)=O.[CH3:19]O>>[C:1]([C:4]1[C:5]([OH:13])=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([O:9][CH3:19])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 108992643-acetyl-2-hydroxybenzoic acid

Product 1

HCID 13037297Methyl 3-acetyl-2-hydroxybenzoateYield 20%

Procedure

To a solution of 3-acetyl-2-hydroxybenzoic acid 32 (3 g, 16.7 mmol) in MeOH (50 mL) was added conc. H2SO4 (3.0 mL. The reaction mixture was heated at reflux for 12 h. After concentration en vacuo, the crude residue was diluted with H2O, basified to pH=8 with aq NaHCO3 and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated to give 38 as a white solid (550 mg, 20% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 12 h
  3. concentrationAfter concentration en vacuo
  4. additionthe crude residue was diluted with H2O
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-df360830e5a64d12a0d55b6271278789
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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