C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/493.5
C07C 69/145 (2006.01) C07C 1/32 (2006.01) C07C 11/12 (2006.01) C07C 29/128 (2006.01) C07C 29/42 (2006.01) C07D 309/12 (2006.01)
Patent
CA 1138473
ABSTRACT OF THE DISCLOSURE: A process is disclosecl for preparing aliphatic com- pounds containing two conjugated double bonds cis-cis or cis- trans, characterized ln that a compound of the general formula Image (I) (in which R is H or an alkyl containing from 1 to 20 carbon atoms, an alkenyl or alkynyl containing from 2 to 20 carbon atoms, a radical containing an ethereal bond or an acetal or ketal group having from 2 to 20 carbon atoms; X is an ester function selected from the class consisting of the acetates, pivaloates, benzoates, mesitoates, or an ethereal function selected from the class con- sisting of ethoxy, methoxy, 2-tetrahydropyranyloxy groups) is reacted with an alkyl-magnesium halide of the general foxmula: Z - Mg - R1 (II) (in which Z is chlorine, bromine, iodine, and Rl is like R with the exeeption of H) in the presence of a cuprous halide selected from the group comprising CuCl, CuBr and CuI, at temperatures ranging from about +10° to -30°C, in the presence of ethyl ether or tetrahydrofuran as solvent, to obtain an aliphatic compound of the general formula: R-CH2-C?C-CH-CH2R1 (III) in which the carbon atoms linked wlth the double bond carry two hydrogen atoms in cis position, and reducing the triple bond of (III) with lithium-aliminum hybride to produce the trans-cis compound, or reducing (III) with dialkylborane or catecholborane to produce the cis-cis compound.
311194
Cassani Giorgio
Massardo Pietro
Piccardi Paolo
Montedison S.p.a.
Robic Robic & Associes/associates
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