Methanol → Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

HRID 1814768Notes

Reaction equation

HRID 1814768 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1[OH:11].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O:7][CH3:17])=[O:6])[C:3]=1[OH:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 67383-Methylsalicylic Acid

Product 1

HCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

Procedure

To a slurry of 3-methylsalicylic acid (200 g) in 600 mL of methanol at −15° is added 65.7 g of concentrated sulfuric acid. The mixture is treated at reflux temperature for 5 days. The reaction mixture is concentrated, and methyl-t-butyl ether (500 mL) and water (250 mL) are added. The ether layer is separated, washed with bicarbonate solution and evaporated to dryness to give methyl 3-methylsalicylate an oil.

Workup

  1. additionThe mixture is treated
  2. temperatureat reflux temperature for 5 days
  3. concentrationThe reaction mixture is concentrated
  4. additionmethyl-t-butyl ether (500 mL) and water (250 mL) are added
  5. customThe ether layer is separated
  6. washwashed with bicarbonate solution
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-48a5bab826a947c394607de71f3d1caf
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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