2,3-Dihydro-thieno(3,4-b)(1,4)dioxin-5,7-dicarboxylic acid → 3,4-Ethylenedioxythiophene

HRID 1270687Notes

Reaction equation

HRID 1270687 reaction equation
[CH2:1]1[CH2:9][O:8][C:7]2[C:3](=[C:4](C(O)=O)[S:5][C:6]=2C(O)=O)[O:2]1>[Cu].C(O)CO>[CH2:1]1[CH2:9][O:8][C:7]2[C:3](=[CH:4][S:5][CH:6]=2)[O:2]1

Participants

4

Reactant 1

HCID 7288412,3-Dihydro-thieno(3,4-b)(1,4)dioxin-5,7-dicarboxylic acid

Product 1

HCID 44218643,4-EthylenedioxythiopheneYield 98.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 174Ethylene GlycolSolvent

Procedure

3,4-Ethylenedioxy-2,5-thiophenedicarboxylic acid (460 g) and a copper powder (69 g) were added to ethylene glycol (1400 g) at room temperature. The reaction mixture was stirred under air for 30 minutes at room temperature, and air was continuously introduced into the reaction mixture. The reaction mixture was then heated at 140° C. for 8 hours. After the reaction was complete, the reaction mixture was purified using the same process as described in Example 1 to obtain 3,4-ethylenedioxythiophene (281 g, purity: 98%).

Workup

  1. additionair was continuously introduced into the reaction mixture
  2. temperatureThe reaction mixture was then heated at 140° C. for 8 hours
  3. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-5434fbfa565d460d8375d7dc18e5f548
Source dataset
uspto-grants-2007_04
Patent number
US07202369B2

Reaction notes

Loading…