Sodium Chloride → HCID 13025622, compound

Participants

Reaction Steps

In a reaction vessel, 5-methyl-2-furylpropylcarbinol (1 g) was charged, and a solution of ZnCl2 (0.9 g) in water (40 ml) was added. The temperature was elevated up to 100° C. to reflux, and several drops of an aqueous 0.1N NaOH solution were added thereto to adjust the pH value to 4.5. By further addition of the same NaOH solution (0.3 ml) thereto, the pH value was not changed but remained at 4.5. The mixture was stirred under reflux for 11 hours, whereby the pH value became 4.2. After cooling, sodium chloride (12 g) was added thereto, and the mixture was extracted with toluene (30 ml) four times. The extract was concentrated at 60° C. under reduced pressure to remove toluene, and the resultant residue was subjected to chromatography with silica gel (10 g) and a mixture of ethyl acetate-n-hexane (1:2 by volume) as the developing solvent to obtain 2-propyl-3-methyl-4-hydroxy-2-cyclopentenone (0.57 g). Yield, 57%.

Provenance & Evidence