Methanol → Methyl 3-hydroxy-2-methylbenzoate

HRID 368343Notes

Reaction equation

HRID 368343 reaction equation
[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].OS(O)(=O)=O.[CH3:17]O>>[OH:1][C:2]1[C:3]([CH3:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2520233-Hydroxy-2-methylbenzoic Acid

Product 1

HCID 12488879Methyl 3-hydroxy-2-methylbenzoateYield 65.6%

Procedure

A solution of 17.98 g (0.118 mol) of 3-hydroxy-2-methylbenzoic acid in 200 mL of MeOH was treated with 2.0 mL of conc. H2SO4 and heated at reflux overnight. The solution was concentrated under reduced pressure and diluted with H2O. The product was collected and recrystallized from MeOH/H2O to give 12.85 g (65.6% yield) of a tan solid, mp 74-75° C. The structure was confirmed by NMR and mass spectroscopy. MS m/z 167 (M+H+).

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. concentrationThe solution was concentrated under reduced pressure
  4. additiondiluted with H2O
  5. customThe product was collected
  6. customrecrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-4866a3be3540436e9a32e711f674394b
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

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