Methanol → 4-(Methoxycarbonyl)-2,6-dimethylbenzoic acid

HRID 345225Notes

Reaction equation

HRID 345225 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([CH3:11])[C:3]=1[C:12]([OH:14])=[O:13].S(=O)(=O)(O)O.O.[CH3:21]O>>[CH3:21][O:9][C:8]([C:6]1[CH:7]=[C:2]([CH3:1])[C:3]([C:12]([OH:14])=[O:13])=[C:4]([CH3:11])[CH:5]=1)=[O:10]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1118Sulfuric AcidHCID 2465942,6-Dimethylterephthalic acid

Product 1

HCID 3482914-(Methoxycarbonyl)-2,6-dimethylbenzoic acid

Procedure

2,6-Dimethyl-1,4-benzenedicarboxylic acid (from Preparation 7) (5.0 g, 26mmol) was suspended in methanol (40 mL), concentrated sulfuric acid (5 mL) was added, and the mixture was heated at reflux for 2 hours. The solution was cooled, and water was added to precipitate the product. Filtration, followed by washing with water (3×) and petroleum ether (3×), and drying at high vacuum gave 2.05 g of the product as a white powder, m.p. 191°-192° C. (ref. W. A. Noyes, cited above).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 hours
  3. temperatureThe solution was cooled
  4. customto precipitate the product
  5. filtrationFiltration
  6. washby washing with water (3×) and petroleum ether (3×)
  7. customdrying at high vacuum

Sources & evidence

ORD record
ord-e2ad9f2185b5485695c7c9853c859902
Source dataset
uspto-grants-1991_10
Patent number
US05055451

Reaction notes

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