Carbon Dioxide → 5-Phenyl-2-Thiophenecarboxylic Acid

HRID 838880

Reaction equation

HRID 838880 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[C:17](=[O:19])=[O:18].CCOCC>O1CCCC1.CCCCCC>[C:1]1([C:7]2[S:8][C:9]([C:17]([OH:19])=[O:18])=[CH:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 3283Diethyl EtherHCID 699992-PhenylthiopheneHCID 178418339Butyllithium

Product 1

HCID 7364945-Phenyl-2-Thiophenecarboxylic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 2-phenylthiophene (16.0 g, 0.1 mole) in 100 ml anhydrous tetrahydrofuran (THF) is treated dropwise with a solution of n-butyl lithium (0.11 mole) in hexane (2 M solution). Thereafter the mixture is stirred for 1 hr. The resulting black solution is poured onto 50 g of solid CO2 covered with ether. When all the CO2 is evaporated, the mixture is treated with 200 ml of water, acidified with 10% HCl and extracted with ether. The extract is washed with 5% NaOH. The latter washings are cooled and rendered acidic with 20% HCl. The resulting precipitate is collected and recrystallized from 100 ml CCl4 to give 5-phenyl 2-thiophenecarboxylic acid, mp 180° C, γmaxCHCl 3 1665 cm-1, as yellow green crystals.

Workup

  1. customWhen all the CO2 is evaporated
  2. additionthe mixture is treated with 200 ml of water
  3. extractionextracted with ether
  4. washThe extract is washed with 5% NaOH
  5. temperatureThe latter washings are cooled
  6. customThe resulting precipitate is collected
  7. customrecrystallized from 100 ml CCl4

Sources & evidence

ORD record
ord-5841dde377d94fdf8f949e9382ca36a8
Source dataset
uspto-grants-1978_06
Patent number
US04093628

Linked notes

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