Thiophene-3,4-dicarboxylic acid → 1H,3H-Thieno[3,4-c]furan-1,3-dione

HRID 2410237Notes

Reaction equation

HRID 2410237 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[C:3]([C:9]([OH:11])=[O:10])=[CH:2]1>C(OC(=O)C)(=O)C>[S:1]1[CH:2]=[C:3]2[C:9]([O:11][C:6](=[O:8])[C:4]2=[CH:5]1)=[O:10]

Participants

3

Reactant 1

HCID 255853Thiophene-3,4-dicarboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of thiophene-3,4-dicarboxylic acid (5.97 g, 34.77 mmol) in acetic anhydride (150 mL) was stirred overnight at 140° C. The reaction mixture was subsequently concentrated to yield thiophene-3,4-dicarboxylic anhydride as a brown solid which was used without further purification. GC-Ms: 154; 1H NMR (400 MHz, CDCl3, ppm) δ: 8.09(s, 2H).

Workup

  1. concentrationThe reaction mixture was subsequently concentrated

Sources & evidence

ORD record
ord-16e4e637936c42e0b5414f578ba45cda
Source dataset
uspto-grants-2014_08
Patent number
US08816035B2

Reaction notes

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