Water → 3,5-Dioxohexanoic acid

참여 물질

반응 단계

To 31 g (0.1M) of 3,4,5-triacetoxybenzoic acid chloride dissolved in 100 ml of tetrahydrofuran was added a solution of 33 g (0.1M) of octadecyloxypropylamine and 10 g (0.1M) of triethylamine dissolved in 50 ml of tetrahydrofuran as the reaction system was cooled with water. Further, the reaction proceeded at room temperature for 4 hours. Thereafter, 200 ml of water was added thereto, and the reaction product was extracted with ethyl acetate. The extract was washed with water and concentrated. Then, it was recrystallized from an ethanol-methanol (250 ml/50 ml) mixture. Thus, the intended triacetate was obtained. Yield 43.5 g (72%). This triacetate was dissolved in a mixed solution consisting of 100 ml of methanol and 50 ml of THF and thereto 2 g of sodium acetate was added. The reaction proceeded at 50° C. for 2 hours. Thereafter, the reaction mixture was neutralized with 24 ml of 1N hydrochloric acid and thereto 300 ml of water was added. Thereupon, crystals separated out. These were filtered off, and recrystallized from 140 ml of chloroform. Thus, 26 g (76%) of the intended compound was obtained. Melting Point 106°-107.5° C.

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