Methanol → Methyl 5-methyl-2-thiophenecarboxylate

HRID 1890522Notes

Reaction equation

HRID 1890522 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH3:15]O>>[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:15])=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 747135-Methylthiophene-2-carboxylic acid

Product 1

HCID 580756Methyl 5-methyl-2-thiophenecarboxylate

Procedure

To a solution of 5-methylthiophene-2-carboxylic acid (F-1) (14.0 g, 0.1 mol) in MeOH (250 mL) was added concentrated H2SO4 (2.0 mL). The reaction mixture was stirred under reflux for 60 h. The solvent was removed in vacuo. Ethyl acetate was added to dilute the reaction mixture. Then the organic solution was washed with a saturated aqueous Na2CO3 solution, and dried over Na2SO4. The solvent was removed to afford the title compound (13.4 g).

Workup

  1. temperatureunder reflux for 60 h
  2. customThe solvent was removed in vacuo
  3. additionEthyl acetate was added
  4. additionto dilute the reaction mixture
  5. washThen the organic solution was washed with a saturated aqueous Na2CO3 solution
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-ed5fc5bd12364163a26b3166d570a05b
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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