Methanol → 4-Methyl-7-propyl-1H-indene

Participants

Reaction Steps

45 ml of a 30 percent strength solution of sodium methanolate in methanol (250 mmol) were initially introduced into the reaction vessel at 0° C., and a mixture of 14.2 g (100 mmol) of 2,5-octanedione and 9 ml (110 mmol) of cyclopentadiene was added in the course of 30 minutes. After the mixture had been stirred at room temperature for 3 hours, it was poured into 300 ml of ice-water and extracted with diethyl ether and the organic phase was dried over magnesium sulfate. The residue which remained after evaporation was chromatographed on silica gel. 6.8 g (39%) of the indene 2 could be isolated with hexane as the mobile phase.

Provenance & Evidence