Methanol → Methyl 3-thiophenecarboxylate

HRID 550549

Reaction equation

HRID 550549 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.S(=O)(=O)(O)O.[CH3:14]O>>[S:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH3:14])=[O:7])=[CH:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 6918Thiophene-3-carboxylic acid

Product 1

HCID 574151Methyl 3-thiophenecarboxylate

Procedure

3-thiophenecarboxylic acid (2.0 g) was dissolved in MeOH (27 mL) and concentrated sulphuric acid (1.5 mL) was added. The reaction mixture was refluxed for 3 hours and 30 min., then concentrated under reduced pressure. A saturated NaHCO3 solution was added and the mixture was extracted with ethyl acetate. The organic phase was dried over Na2SO4 and concentrated in vacuo to give 1.98 g of the title compound as a colourless liquid which was used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours and 30 min.
  2. concentrationconcentrated under reduced pressure
  3. additionA saturated NaHCO3 solution was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d3e5106c7154efaadb5a663b4df7f11
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Linked notes

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