Salicylic Acid → Methyl Salicylate

HRID 1259014Notes

Reaction equation

HRID 1259014 reaction equation
OS(O)(=O)=O.[C:6]([OH:15])(=[O:14])[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[OH:9].O.[CH3:17]O>>[OH:9][C:8]1[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=1[C:6]([O:15][CH3:17])=[O:14]

Participants

5

Reactant 4

HCID 338Salicylic AcidHCID 887MethanolHCID 962WaterHCID 1118Sulfuric Acid

Product 1

HCID 4133Methyl SalicylateYield 98%

Procedure

H2SO4 (4.0 mL, 74.63 mmol) was added to a solution of salicylic acid (5.0 g, 36.20 mmol) in MeOH (60 mL). The reaction mixture was refluxed for 20 h, allowed to reach r.t., poured into H2O (100 mL) and extracted with CH2Cl2 (120 mL). The organic layer was dried over Na2SO4 (anhydrous), filtered and concentrated. The crude residue was flash chromatographed on SiO2 (5% EtOAc/hexanes) to furnish 5.44 g of methyl 2-hydroxybenzoate (colourless oil, yield: 98%).

Workup

  1. temperatureThe reaction mixture was refluxed for 20 h
  2. customto reach r.t.
  3. extractionextracted with CH2Cl2 (120 mL)
  4. dry with materialThe organic layer was dried over Na2SO4 (anhydrous)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on SiO2 (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8b4161673fb04992a834e642cd2733a2
Source dataset
uspto-grants-2013_06
Patent number
US08466197B2

Reaction notes

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