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

1981-10-06

Trousof, Natalie

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

568875, C07D31172, C07C 2702

Patent

active

042934974

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 on 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: 2995600 (1961-08-01), Webb
patent: 3031442 (1962-04-01), Webb
patent: 3076839 (1963-02-01), Webb
patent: 3825607 (1974-07-01), Descoins et al.
patent: 3948803 (1976-04-01), Carney
Nakagawa, Chem. Abst., vol. 66, #28937x, (1967).
Svishchuk et al., Chem. Abst., vol. 80, #59820x, (1974).

Affiliated with

Also associated with

Rating

Coupling reaction involving a grignard and allylic halide does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Coupling reaction involving a grignard and allylic halide, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Coupling reaction involving a grignard and allylic halide will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1206194