Methanol → Methyl 3-hydroxy-2-methylbenzoate

HRID 1386410Notes

Reaction equation

HRID 1386410 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-494436ce2b244d6886c57e831f1f6b78
Source dataset
uspto-grants-2001_07
Patent number
US06265422B1

Reaction notes

Loading…