Coupling reaction involving a Grignard and allylic halide

Details Coupling reaction involving a Grignard and allylic halide Coupling reaction involving a Grignard and allylic halide

1980-03-18

1981-09-29

Davis, Curtis R.

Chemistry of hydrocarbon compounds

Compound or reaction product mixture

568388, 568417, 568687, 568875, 570135, 570189, 585600, 585900, C07C 1121

Patent

active

042924545

ABSTRACT:
Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.

REFERENCES:
patent: 2783257 (1957-02-01), Surmatis et al.
patent: 2809215 (1957-10-01), Surmatis et al.
patent: 3453317 (1969-07-01), Marbet et al.
patent: 3493619 (1970-02-01), Marbet et al.
patent: 3574715 (1971-04-01), Marbet et al.
patent: 3859374 (1975-01-01), Komatsu et al.
patent: 4168271 (1979-09-01), Cardenas et al.
patent: 4221742 (1980-09-01), Cardenas et al.
Nazarov et al., Izvest. Akad. Nauk SSSR., otdel. Khim. Nauk 1957, 1267-1270.
Nazarov et al., Zhur. Obshehei Khim. 28, 1444-1458 (1958).
Ofner et al., Helv. Chim Acta. 42, 2577-2584 (1959).
Teisseire et al., Riv. Ital. Essenze-Profumi-Pirnte Offic.-Aromi-Saponi-Cosmet. 45(8), 392-403 (1963).
Julia et al., Bull. Soc Chim. France 1960, 1072-1079.
Dare et al., Chem. Ind. (London) 1966 (15), 629-630.

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