An improved electrochemical method for the synthesis of some benzofuran derivatives.
Electrochemical oxidation of catechol and some 3-substituted catechols (1a--c) has been studied in the presence of 2-chloro-5,5-dimethyl-1,3-cyclohexanedione (3) in aqueous solution using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from catechols (1a--c) participate in a Michael addition reaction with 2-chloro-5,5-dimethyl-1,3-cyclohexanedione (3) with consumption of only two electrons per molecule of (1a--c) to from the corresponding benzoforans (10a--c). The electrochemical synthesis of benzofurans has been successfully performed at a carbon rod electrode and in an undivided cell with high yields and purity.
Davarani
Saied Saeed Hosseiny
SS
Department of Chemistry, Shahid Beheshti University, Tehran, Iran.
Najafi
Nahid Mashkouri
NM
Ramyar
Somayyeh
S
Masoumi
Leila
L
Shamsipur
Mojtaba
M
D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D002396:Catechols / Q000737:chemistry; D004563:Electrochemistry / Q000379:methods*; D015394:Molecular Structure
D001572:Benzofurans; D002396:Catechols