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Abstract

Abstract 1,154,191. Unsaturated acid esters. BAT. TELLE DEVELOPMENT CORP. 16 May, 1967 [6 June, (3)], No. 22568/67. Heading C2C. [Also in Divisions C5 and G2] The dimethyl ester of 10.12-docosadiyne dioic acid is prepared by treating 10-undecynoic acid BCl 3 /methanol solution and reacting the methyl-10-undecynoate produced with N,N,N<SP>1</SP>,N<SP>1</SP>- tetramethyl ethylene diamine, methanol and cuprous chloride and oxygen. The diethyl ester of 11,13-tetracosadiynedioic acid is pepared similarly. Dimethyl ester of 11,13-tetracosa diynedioic acid is prepared by treating #- bromodecanoic acid with lithium acetylide ethylene diamine complex/sulphur dioxide to give 11-dodecynoic acid which is then processed as for 10-undecynoic acid above. Dimethyl ester of 4,6-decadiynedioic acid by treating the corresponding acid with BCl 3 /methanol. Dimethyl ester of 7,9-hexadecadiyne dioic acid, dicyclohexyl ester of 10,12-docosadiyne dioic acid and dibenzyl ester of 10,12-docosa diyne dioic acid are prepared similarly. The monomethyl ester of 4,6-decadiyne dioic acid is prepared by treating the diester with barium hydroxide. Monomethyl 11,13-tetracosa diynedioic acid, monomethyl 11,13-tetracosadiynedioic acid and monomethyl 10,12-docosadiynedioic acid, which when treated with kOH gives its monopotassium salt, are obtained similarly. The monocyclohexyl ester of 10,12-docosadiyne dioic acid is obtained by treating a mixture of the free acid and diester with p-toluene sulphonic acid. Monobenzyl ester of 10,12-docasadiyne dioic acid is obtained by treating the free acid with thionylchloride and then benzyl alcohol. Monopentyl ester of 10,12-docosodiyne dioic acid is obtained by treating the free acid with ptoluene sulphonic acid/neopentyl alcohol.

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