Sulfuric Acid → Methyl 4-methoxythiophene-3-carboxylate

HRID 2107618Notes

Reaction equation

HRID 2107618 reaction equation
[C:1]([O:4][C:5]1[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][S:8][CH:9]=1)(=O)C.S(=O)(=O)(O)O>CO>[CH3:1][O:4][C:5]1[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][S:8][CH:9]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12520003Methyl 4-acetoxythiophene-3-carboxylate

Product 1

HCID 2778377Methyl 4-methoxythiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-acetoxy-3-thiophenecarboxylate (81 g, 0.40 mol) and concentrated sulphuric acid (5 ml) in methanol (1.25 l) was heated under reflux for 3 days. The solvent was evaporated and the residue diluted with water (300 ml) and extracted with ether (5 times). The ether extracts were combined, washed with 1N sodium hydroxide (3 times) and dried over sodium sulfate. Evaporation of the solvent gave the title compound, 52 g, m.p. 66°-68° (lit. m.p.68°-70°).

Workup

  1. temperatureunder reflux for 3 days
  2. customThe solvent was evaporated
  3. additionthe residue diluted with water (300 ml)
  4. extractionextracted with ether (5 times)
  5. washwashed with 1N sodium hydroxide (3 times)
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5378a3a2a5314ef488fde81e9a19b0ee
Source dataset
uspto-grants-1990_06
Patent number
US04935431

Reaction notes

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