Manufacture of cycloalkenylpolyene esters

C - Chemistry – Metallurgy – 07 – C

Patent

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C07C 403/12 (2006.01) C07C 51/00 (2006.01) C07C 67/00 (2006.01) C07C 67/29 (2006.01) C07C 67/333 (2006.01) C07C 69/16 (2006.01) C07C 403/06 (2006.01) C07C 403/10 (2006.01)

Patent

CA 2299744

A process for the manufacture of a retinyl acylate of the formula Image wherein R1 signifies optionally substituted C1-23-alkyl; C2-23-alkenyl featuring 1 to 5 double bonds; optionally aromatically substituted phenyl-C1-6-alkyl; or optionally substituted phenyl, is characterized by treating a compound of the formula Image wherein R1 has the significance given above and R2 signifies hydrogen or COR1, with an agent which is an acid anhydride or a complex of sulphur trioxide, as specified in the description, in the presence of dimethylformamide as a solvent and simultaneously as a weak base. In addition to dimethylformamide an aprotic organic solvent may optionally be present, particularly an aliphatic hydrocarbon, an optionally alkyl- substituted alicyclic hydrocarbon, an aromatic hydrocarbon, a halogenated aliphatic hydrocarbon, a nitrated aliphatic hydrocarbon, an aliphatic ether, a cyclic ether, an aliphatic nitrite, an aliphatic amine, an aliphatic or alicyclic amide, dimethyl sulphoxide, tetramethylene sulphone, or a mixture of one or more of such solvents. The products are useful as intermediates for the manufacture of compounds of the vitamin A group or in certain cases as the compounds themselves.

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