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

HRID 1270688

Reaction equation

HRID 1270688 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>C(=O)([O-])[O-].[Cu+2].CN(C=O)C>[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 95.7%

Reagents, catalysts & solvents 2

HCID 14452Copper carbonateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

3,4-Ethylenedioxythiophene-2,5-dicarboxylic acid (230 g) and basic copper carbonate (23 g) were added to DMF (600 g) at room temperature. While air was slowly introduced to the reaction mixture, it as heated at 120° C. for 5 hours. After cooling, the reaction mixture was purified using the same process as described in Example 1 to obtain 3,4-ethylenedioxythiophene (136 g, purity: 97%).

Workup

  1. additionWhile air was slowly introduced to the reaction mixture, it
  2. temperatureAfter cooling
  3. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-c0afad15774543e79cc67598afc32074
Source dataset
uspto-grants-2007_04
Patent number
US07202369B2

Linked notes

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