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

1977-04-13

1981-09-29

Davis, Curtis R.

Chemistry of hydrocarbon compounds

Unsaturated compound synthesis

From nonhydrocarbon feed

585469, C07C 126

Patent

active

042924596

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: 3948803 (1976-04-01), Carney
Kharasch et al., "Grignard Reactions of Nonmetallic Substances" (1954), Prentice-Hall, New York pp. 1157 to 1165.
Tamura et al., "Journal of Organometallic Chemistry", 42 (1972) pp. 205 to 210.

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-1234894