p-Toluenesulfonic acid → Ethyl 4-oxotetrahydrothiophene-3-carboxylate

HRID 1903639Notes

Reaction equation

HRID 1903639 reaction equation
[O:1]=[C:2]1[CH:6]([C:7]([O:9][CH3:10])=[O:8])[CH2:5][S:4][CH2:3]1.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[O:1]=[C:2]1[CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:5][S:4][CH2:3]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 984243-Thiophenecarboxylic acid, tetrahydro-4-oxo-, methyl ester

Product 1

HCID 310629Ethyl 4-oxotetrahydrothiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 parts by weight of methyl 3-keto-1,5-dihydrothiophene-4-carboxylate, 57.8 parts by weight of ethanol and 1 part by weight of p-toluenesulfonic acid are refluxed for 50 hours, and the mixture is then distilled. 17.1 parts by weight of ethyl 3-keto-1,5-dihydrothiophene-4-carboxylate of melting point 106°-109° C./1.3 mbar are obtained.

Workup

  1. distillationthe mixture is then distilled

Sources & evidence

ORD record
ord-39f68d43f51041e3867a14821280d6d7
Source dataset
uspto-grants-1984_03
Patent number
US04437878

Reaction notes

Loading…