Acetone → HCID 21402622, compound

Participants

Reaction Steps

A mixture of 23.4 parts of 5-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylic acid, ethyl ester, 19.8 parts of 1-iodo-3-methybutane, 11.65 parts of anhydrous potassium carbonate and 500 parts of acetone was refluxed for thirteen days. After cooling, the reaction mixture was filtered and the volatile components of the filtrate were removed by evaporation to give a residue which was dissolved in chloroform. The chloroform extract was washed with cold N sodium hydroxide solution, then with water and evaporated. The oily residue obtained was stirred in sodium bicarbonate solution at 100°C for two hours. After cooling, the solution was extracted with chloroform and the aqueous layer was separated. The aqueous extract was acidified with 2N hydrochloric acid and the mixture was extracted with chloroform. Evaporation of the chloroform gave 8.79 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