Acetic Anhydride → 1H,3H-Thieno[3,4-c]furan-1,3-dione

HRID 531428

Reaction equation

HRID 531428 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>>[C:6]1(=[O:8])[C:4]2=[CH:5][S:1][CH:2]=[C:3]2[C:9](=[O:10])[O:11]1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 255853Thiophene-3,4-dicarboxylic acid

Product 1

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

Procedure

In a 250 mL single-neck round-bottom flask equipped with reflux condenser, 3,4-thiophenedicarboxylic acid (Frontier Scientific, 4.000 g, 0.02325 mol) was heated to 120° C. with acetic anhydride for 6 hours. The reaction was then cooled to room temperature and the solvent was removed under reduced pressure to yield a dark brown solid. The crude product was recrystallized from toluene to yield pale yellow needles in quantitative yield.

Workup

  1. customIn a 250 mL single-neck round-bottom flask equipped
  2. temperaturewith reflux condenser
  3. customthe solvent was removed under reduced pressure
  4. customto yield a dark brown solid
  5. customThe crude product was recrystallized from toluene
  6. customto yield pale yellow needles in quantitative yield

Sources & evidence

ORD record
ord-0c388784e8e84e07bbfc2cc9cb2978ed
Source dataset
uspto-grants-2016_05
Patent number
US09355787B2

Linked notes

Loading…