Hydrochloric Acid → HCID 13036788, compound

Participants

Reaction Conditions

Reaction Steps

In a reaction vessel, water (40 ml) and 5-methyl-2-furyl-n-butylcarbinol (0.5 g) were charged, and the pH value was regulated to 5 with an aqueous 1 N NaOH solution and an aqueous 1 N HCl solution. The temperature was elevated up to 100° C. to reflux, and the mixture was stirred under reflux for 30 hours while maintaining a pH value of 5 to 5.5 by the addition of an aqueous 1 N NaOH solution and an aqueous 1 N HCl solution. After cooling to 40° C., the reaction mixture was neutralized with an aqueous 1 N NaOH solution, and sodium chloride (12 g) was added thereto. The mixture was extracted with toluene (40 ml) five times. From the extract, toluene was removed by distillation at 60° C. under reduced pressure to give an oily substance (0.48 g), which was subjected to a thin layer chromatography on silica gel with a mixture of ethyl acetate-n-hexane (1:2 by volume) as the developing solvent. The objective part of the silica gel layer was collected by scraping and eluted with ethyl acetate. The silica gel was eliminated by filtration, and the filtrate was concentrated to obtain 2-n-butyl-3-hydroxy-3-methyl-4-cyclopentenone (3.5 g). Yield, 70%. NMR spectrum (CCl4, internal standard TMS, δ ppm, 60 MHz): 7.25 (d, 1H, 4-H); 5.85 (d, 1H, 5-H); 3.63 (broad s, 1H, 3--OH); 2.20 (m, 1H, 2-H); 1.25 (s, 3H, 3-CH3).

Provenance & Evidence