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Carboxylic Ortho Acid Derivatives: Preparation and Synthetic by Robert H. De Wolfe PDF

By Robert H. De Wolfe

ISBN-10: 012214550X

ISBN-13: 9780122145506

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In spite of these limitations a number of ortho esters have been synthesized from ketene acetals, and several of them have been prepared in no other way. These include trimethyl orthodiphenylacetate (218), divinylethyl orthoacetate (205), divinyl-2-chloroethyl orthoacetate (205), three divinyl-2-nitroalkyl orthoacetates (100), trimethyl dimethoxyorthoacetate (143), triethyl 3,3-diethoxyorthopropionate (219), triethyl ortho-3-methyl3-butenoate (220), 2-methoxy- and 2-ethoxy-2-chloromethyl-l,3-dioxolanes (98, 209), 2-methoxy- and 2-ethoxy-2-dichloromethyl-l,3-dioxolanes (209, 308), and 2-methoxy-2-benzyl-l,3-dioxolane (209).

Similar 1,1-diacyloxy-1-alkoxyethanes are transient intermediates in the 53 SYNTHESIS OF ACYLOXY ORTHO ESTERS conversion of carboxylic acids to anhydrides by reaction with alkoxyacetylenes (90, 263, 356). CH (C0 H) + HC=COCH 2 2 2 3 • < X ( 3) 9 Lead tetraacetate oxidation of dibutyl ether gave a mixture of products containing 1 -butoxy-1,1 -diacetoxybutane and 1 -(1 -acetoxybutoxy)-1,1 -diacetoxybutane (158). Three methods of preparing acyloxy ortho esters in which the acyloxy group is incorporated into a lactone ring have been reported.

4250 (20°) 3 93a Η OCH IW X 3 CH, /—Ο OCH 3 V _ o / X H — 1 . 0010 1 1 2,5 275 309, 351 6a, 8a, 42, 232a, 233, 283. 344. 4425 — 11 153a 3 x 1. 5°-44710 ^-O Density d 6 C H s oc,H Refractive index /~°\/ 5 H K \ — ΟXOC H 2 6 1.

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Carboxylic Ortho Acid Derivatives: Preparation and Synthetic Applications by Robert H. De Wolfe

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