Methanol → Methyl 3-hydroxy-2-methylbenzoate

HRID 1859815Notes

Reaction equation

HRID 1859815 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 L 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-d2918f998fe5448cb5749d7ba9961abc
Source dataset
uspto-grants-2003_03
Patent number
US06528535B2

Reaction notes

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