1,5-Diphenylpentan-3-one → Methyl formate

Participants

Reaction Steps

To a suspension of sodium methoxide (6 g) in ethylether (80 ml), a mixture of 1,5-diphenyl-3-pentanone (24 g, 0.1 mole) obtained in above (1) and methyl formate (6.7 g, 0.11 mole) was added dropwise at 1°-2° C., stirring was continued for 1 hour at the same temperature and allowed to stand overnight at room temperature. The reaction mixture was poured into cold H2O (300 ml), and aqueous layer was separated, acidified to ph 1 with 5% sulfuric acid and extracted with ethylether (100 ml×3). The organic layer was separated, washed with H2O (100 ml×2), dried over anhydrous MgSO4 and evaporated to give 12.7 g of the title compound as a pale yellow oil. The product was found to have keto-form and enol-form in molar ratio of ca. 1:1 based on 1HNMR.

Provenance & Evidence