Carbon Dioxide → Benzo(b)thiophene-2-carboxylic acid

HRID 2052455Notes

Reaction equation

HRID 2052455 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][S:9][C:4]2=[CH:3][CH:2]=1.[Li+].CCC[CH2-].[C:15](=[O:17])=[O:16]>CCOCC>[CH:1]1[CH:6]=[C:5]2[CH:7]=[C:8]([C:15]([OH:17])=[O:16])[S:9][C:4]2=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 7221Benzo(B)ThiopheneHCID 61028n-Butyl lithium

Product 1

HCID 95864Benzo(b)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Thionaphthene was treated in a carboxylation reaction in accordance with the procedure described by D. A. Shirley and M. D. Cameron, in J. Am. Chem. Soc., 72, 2788, 1950 using N-butyllithium in ether, followed by carbonation with dry ice, and hydrolysis to the acid. The product had a melting point of 238°-239° C.

Sources & evidence

ORD record
ord-a511c9a7bb42430a87ba8d3ae381032f
Source dataset
uspto-grants-1980_01
Patent number
US04185108

Reaction notes

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