Chloroacetyl chloride → Thiophene-3,4-dicarboxylic acid

Reaction equation

ClCC(Cl)=[O:4].[S:6]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:8]2=[CH:7]1)=[O:12]>>[S:6]1[CH:10]=[C:9]([C:11]([OH:4])=[O:12])[C:8]([C:14]([OH:13])=[O:15])=[CH:7]1

Participants

Reactant 2

HCID 6577Chloroacetyl chloride

HCID 3156081H,3H-Thieno[3,4-c]furan-1,3-dione

Product 1

HCID 255853Thiophene-3,4-dicarboxylic acid

Procedure

A 25.5 g. portion of 3,4-thiophenedicarboxylic acid {prepared by the method of Kornfeld and Jones [J. Org. Chem., 19, 1671 (1954)]} is suspended in 50 ml. of chloroacetyl chloride and is heated at reflux for 5.5 hours. Excess chloroacetyl chloride is distilled under reduced pressure. The residue is poured into 100 ml. of water and the resulting crystals are collected to yield 16.1 g. of 3,4-thiophenedicarboxylic anhydride.

Workup

temperatureat reflux for 5.5 hours
distillationExcess chloroacetyl chloride is distilled under reduced pressure
additionThe residue is poured into 100 ml
customof water and the resulting crystals are collected
customto yield 16.1 g

Sources & evidence

ORD record: ord-cdd40e584b9e4651ba74e24770d441ee
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04259476

Reaction notes

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