Diketene → HCID 20360652, compound

Participants

Reaction Steps

33.6 g (0.4 mol) of diketene were added drop by drop, while stirring at -30° C, to 37.6 g (0.2 mol) of 2,6-dimethoxynaphthalene in 200 ml of anhydrous hydrofluoric acid and the mixture was stirred for another 8 hours at said temperature. The hydrogen fluoride was distilled off under reduced pressure at a temperature of the still of -30° C and the residue washed until it was free from acid. After sublimation of unreacted starting product (11 g = 71 % conversion) colorless crystals of 1-acetoacetyl-2,6-dimethoxynaphthalene melting at 88° C were obtained by column chromatography (silica gel, 0.065 - 0.2 mm, CH2Cl2) in an amount of 35 g (90 % calculated on 2,6-dimethoxynaphthalene).

Provenance & Evidence