1-Iodo-3-methylbutane → HCID 21402622, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of 21.87 parts of ethyl 5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, thallium salt and 99 parts of 1-iodo-3-methylbutane was refluxed for one hour. After cooling, chloroform was added to the reaction mixture and the insoluble thallium salts were removed by filtration. The chloroform filtrate was washed with cold N sodium hydroxide solution, then washed with water and the volatile components were removed by evaporation. Sodium bicarbonate solution was added to the oily residue obtained and the mixture was stirred at 100°C for two hours. After cooling, the solution was extracted with chloroform and the aqueous layer was separated. This aqueous extract was acidified with 2N hydrochloric acid and the solid which precipitated was collected by filtration, washed with water and dried to give 6.16 parts of 5-(3-methyl-n-butoxy)-4-oxo-4H-1-benzopyran-2-carboxylic acid, m.p. 181°-183°C (after crystallisation from ethyl acetate/light petroleum).

Provenance & Evidence