Carbon Dioxide → 2,5-Thiophenedicarboxylic acid

HRID 838871

Reaction equation

HRID 838871 reaction equation
I[C:2]1[S:3][C:4](I)=[CH:5][CH:6]=1.C([Li])CCC.[C:13](=[O:15])=[O:14].S(=O)(=O)(O)[OH:17].CC[O:23][CH2:24]C>O.O1CCCC1>[S:3]1[C:4]([C:13]([OH:15])=[O:14])=[CH:5][CH:6]=[C:2]1[C:24]([OH:23])=[O:17]

Participants

8

Reactant 5

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 693682,5-DiiodothiopheneHCID 178418339Butyllithium

Product 1

HCID 202732,5-Thiophenedicarboxylic acidYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.5 g. of 2,5-diiodothiophene in 5 ml. of anhydrous tetrahydrofuran and 5 ml. of anhydrous ether at -5°, under nitrogen, is added dropwise over the period of one-half hour 14.92 ml. of 1.5 M n-butyllithium. After standing for two hours at 0°, carbon dioxide gas is added to the mixture for one-half hour at 0° and one-half hour at 10°. The reaction mixture is stirred at room temperature overnight. Water is added, the aqueous layer is acidified with 2N sulfuric acid, and the solution is then extracted with ether, the combined organic phases are washed with water and brine, dried over calcium sulfate, filtered and the solvent removed to yield 2,5-thiophenedicarboxylic acid (about 60% pure).

Workup

  1. extractionthe solution is then extracted with ether
  2. washthe combined organic phases are washed with water and brine
  3. dry with materialdried over calcium sulfate
  4. filtrationfiltered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-9d0ebfaef5924de18cd24edb2b897718
Source dataset
uspto-grants-1978_06
Patent number
US04093622

Linked notes

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