专利号:US-4125735-A 优先权日:1975-03-20 标 题 :Synthesis of esters of acetylenic alcohols 发明人:CLOSE RALPH E; OROSHNIK WILLIAM 权利人:SCM CORP 摘要:A process for the synthesis of perfume products, Vitamin E and intermediates described herein involving a coupling reaction. For instance, a process for the synthesis of dehydrophytol and Vitamin E comprising forming a C15 acetylene from hexahydropseudoionone and then coupling said acetylene with 1-acetoxy-4-chloro-3-methylbut-2-ene to form a C20 acetoxy-enyne. The latter is readily subjected to partial hydrogenation and saponification in that order to form a dehydrophytol, a useful intermediate for the synthesis of Vitamin E and other products.
专利号:US-4039591-A 优先权日:1975-03-20 标 题:Synthesis of dehydrophytol and Vitamin E 发明人:CLOSE RALPH E; OROSHNIK WILLIAM 权利人:SCM CORP 摘要:A process for the synthesis of dehydrophytol and Vitamin E comprising forming a C15 acetylene from hexahydropseudoionone and then coupling said acetylene with 1-acetoxy-4-chloro-3-methylbut-2-ene to form a C20 acetoxy-enyne. The latter is readily subjected to partial hydrogenation and saponification in that order to form a dehydrophytol, a useful intermediate for the synthesis of Vitamin E and other products.
专利号:US-4115466-A 优先权日:1975-10-16 标题:Synthesis of acetylenic compounds useful in preparing dehydrophytols and Vitamin E 发明人:CLOSE RALPH E; OROSHNIK WILLIAM 权利人:SCM CORP 摘要:A process for the synthesis of an acetylenic hydrocarbon from an acetylenic carbinol which involves first replacing the hydroxyl group of the carbinol with a halogen to form a propargylic halide, dehalogenating the propargylic halide to form an allene, and isomerizing said allene to the desired acetylene. The present invention is particularly useful in the synthesis of Vitamin E.
专利号:US-4035425-A 优先权日:1973-04-23 标 题 :Synthesis of Vitamin A, intermediates and conversion thereof to Vitamin A 发明人:OROSHNIK WILLIAM 权利人:SCM CORP 摘要:A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C20 skeleton. By semi-hydrogenation, the acetylenic bond on the C20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.
专利号:US-4092366-A 优先权日:1975-04-10 标题:Synthesis of Vitamin A, intermediates and conversion thereof to Vitamin A 发明人:OROSHNIK WILLIAM 权利人:SCM CORP 摘要:A synthesis of novel Vitamin A intermediates from betaionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C20 skeleton. By semi-hydrogenation, the acetylenic bond on the C20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.
专利号:US-3949006-A 优先权日:1972-04-24 标题:Synthesis of vitamin A, intermediates and conversion thereof to vitamin A 发明人:OROSHNIK WILLIAM 权利人:SCM CORP 摘要:A synthesis of novel Vitamin A intermediates from betaionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C20 skeleton. By semi-hydrogenation, the acetylenic bond on the C20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.