Methanol → Methyl 3,4-dimethylbenzoate

HRID 1940020Notes

Reaction equation

HRID 1940020 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH3:17])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 120733,4-Dimethylbenzoic acid

Product 1

HCID 520902Methyl 3,4-dimethylbenzoateYield 97%

Procedure

3,4-Dimethylbenzoic acid (64.4 g, 429 mmol) was dissolved in methanol (600 ml), and sulfuric acid (9 ml) was added, which was followed by reflux under heating for 5 hours. The reaction mixture was concentrated to 160 ml and water was added. The mixture was extracted with ethyl acetate, and the organic extract was washed successively with water, 10% aqueous sodium hydroxide solution and saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to give 68.0 g of methyl 3,4-dimethylbenzoate (yield 97%).

Workup

  1. temperatureby reflux
  2. temperatureunder heating for 5 hours
  3. concentrationThe reaction mixture was concentrated to 160 ml and water
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate
  6. extractionthe organic extract
  7. washwas washed successively with water, 10% aqueous sodium hydroxide solution and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-f5d107300bfe4874a03581cf49a0bca2
Source dataset
uspto-grants-1997_12
Patent number
US05698580

Reaction notes

Loading…