Chloroacetyl chloride → Thiophene-3,4-dicarboxylic acid

HRID 128352

Reaction equation

HRID 128352 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

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 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

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

Sources & evidence

ORD record
ord-cdd40e584b9e4651ba74e24770d441ee
Source dataset
uspto-grants-1981_03
Patent number
US04259476

Linked notes

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