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    • 4. 发明授权
    • Methods for making 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide, ester of omega-hydroxy-(&ohgr;-3)-ketoaliphatic acid, and derivatives thereof
    • 制备2-(ω-烷氧基羰基烷酰基)-4-丁醇酯,ω-羟基 - (ω-3) - 酮脂肪酸的酯及其衍生物的方法
    • US06475133B2
    • 2002-11-05
    • US09894014
    • 2001-06-28
    • Hideaki TakaokaSigeru WadaNobuhiko ItoAkio HasebeShinzo ImamuraHideo Muraoka
    • Hideaki TakaokaSigeru WadaNobuhiko ItoAkio HasebeShinzo ImamuraHideo Muraoka
    • C07C5100
    • C07D307/33C07C51/43C07C67/32C07C69/716C07C59/215
    • In industrial production of &ohgr;-hydroxyaliphatic acid being an important intermediate for large cyclic lactone-based perfumes, using dicarboxylate ester which is inexpensive and readily obtainable, a method, with high yield and improved selectively, for making a 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and an alkaline metal salt thereof, an ester of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid as a novel compound and a derivative thereof, and a method for making the same are provided. Condensation reaction of &ggr;-butyrolactone with a dicarboxylate ester represented by the general formula (1) ROOC(CH2)nCOOR wherein n is an integer of 7 to 13 and R is an alkyl group forms a condensation solution containing an alkaline metal salt of 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide represented by the general formula (3): wherein n is an integer of 7 to 13, R is an alkyl group, and M is an alkaline metal; the solution is extracted with water or an aqueous alkaline solution and subjected to hydrolysis and decarboxylation to form an alkaline metal salt of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid represented by the general formula (5): wherein n is an integer of 7 to 13 and M is an alkaline metal; and the compound is selectively and effectively separated and recovered and then acidified to form an &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid represented by the general formula (10): wherein n is an integer of 7 to 13.
    • 在工业生产中,ω-羟基脂肪酸是大环内酯基香料的重要中间体,使用廉价且易于获得的二羧酸酯,可以制备2-(ω-烷氧羰基烷酰基) -4-丁醇酸及其碱金属盐,作为新化合物的ω-羟基 - (ω-3) - 酮脂肪酸的酯及其衍生物及其制备方法。 (1)ROOC(CH 2)n COOR表示的二羧酸酯的丁内酯,其中n为7〜13的整数,R为烷基,形成含有2-(ω-烷氧基羰基烷酰基)的碱金属盐的缩合溶液, 由通式(3)表示的4-丁醇酯:其中n为7〜13的整数,R为烷基,M为碱金属; 溶液用水或碱性水溶液萃取,并进行水解和脱羧,形成由通式(5)表示的ω-羟基 - (ω-3) - 酮脂肪酸的碱金属盐:其中n为整数 为7〜13,M为碱金属; 选择性且有效地分离和回收化合物,然后酸化以形成由通式(10)表示的ω-羟基 - (ω-3) - 酮脂肪酸:其中n为7至13的整数。