Methanol → Methyl 5-methyl-2-thiophenecarboxylate

HRID 876775Notes

Reaction equation

HRID 876775 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-a60fd95572524ae3a680fc1685c08902
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

Loading…