Preparation of polyenes

C - Chemistry – Metallurgy – 07 – C

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C07C 403/00 (2006.01) C07C 1/32 (2006.01) C07C 11/21 (2006.01) C07C 45/60 (2006.01) C07C 47/21 (2006.01) C07D 319/06 (2006.01)

Patent

CA 2071772

O.Z. 0050/42562 Abstract of the Disclosure: An improved process for the preparation of polyenes by the Julia reaction comprises carrying out the allylation of the anion of an allyl aryl sulfone generated a strong base, and the elimination of arylsulfinic acid to form a double bond in the same inert polar solvent which is immiscible with water, preferably in a ketone of the formula I R1-CO-R2 (I) where R1 and R2 are each straight-chain or branched alkyl of 2 to 4 carbons, or R1 and R2 together are tetra- methylene or pentamethylene. The process is particularly important for the preparation of vitamin A derivatives. In the preparation of vitamin A aldehyde, for example, it is advantageous to use the same alkali metal alcoholate as strong base in both stages so that the conversion can be carried out as one-pot reaction.

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