Sulfuric Acid → 3-(Methoxycarbonyl)-5-methylbenzoic acid

HRID 2071122

Reaction equation

HRID 2071122 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14]1COCC1.OS(O)(=O)=O>CO.O>[CH3:14][O:12][C:11]([C:4]1[CH:5]=[C:6]([CH:10]=[C:2]([CH3:1])[CH:3]=1)[C:7]([OH:9])=[O:8])=[O:13]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 8028TetrahydrofuranHCID 681375-Methylisophthalic acid

Product 1

HCID 72108363-(Methoxycarbonyl)-5-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To 5-methylisophthalic acid (Aldrich, 5 g, 27.7) in MeOH (37.5 ml)/THF (112.5 ml), conc. H2SO4 (1.25 ml) was added and stirred at 65° C. for 8 h. Reaction mixture was cooled to room temperature and solvent removed. Then reaction mixture was diluted with water and extracted with ethylacetate. Crude residue was column chromatographed to yield 2.5 g of 3-(methoxycarbonyl)-5-methylbenzoic acid as a white solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customsolvent removed
  4. customThen reaction mixture
  5. extractionextracted with ethylacetate
  6. customchromatographed

Sources & evidence

ORD record
ord-485575d1876a408384cb42f3c6a4aacf
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Linked notes

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