Cyclohexene → 3-Methyl-2,3,4,5,6,7-hexahydro-1H-inden-1-one

Participants

Reaction Steps

Cyclohexene (27.3 g, 0.33 mol), crotonic acid (28.7 g, 0.33 mol) and polyphosphoric acid (300 ml) were mechanically stirred under a nitrogen atmosphere at 60° C. for 30 minutes. The slurry was poured into water and the aqueous solution extracted with diethyl ether. The diethyl ether extract was washed successively with a 10 percent NaHCO3 solution and a saturated NaCl solution. The organic extract was then dried over anhydrous MgSO4. The solution was then filtered and the solvent removed under reduced pressure. The crude product was then purified via vacuum distillation (bp 87°-92° C. at 5 mm) to give 32.6 g (66 percent) of purified material.

Provenance & Evidence