Processes for producing alkenals and intermediates therefor

Details Processes for producing alkenals and intermediates therefor Processes for producing alkenals and intermediates therefor

1977-04-18

1978-05-09

Thomas, Jr., James O.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07C 4720

Patent

active

040886964

ABSTRACT:
Processes for producing novel 2-alkylidene-3-alkynals and 2-alkylidene-3-alkenals which comprise reacting an alkyl metallo acetylide with a dialkoxy acetonitrile or a dialkoxy dialkyl acetamide to form an imine salt, hydrolyzing the imine salt to form a 1,1-dialkoxy-3-alkyn-2-one, alternatively (a) first treating the alkynone with an alkylidene tri-substituted phosphorane or an alkylidene phosphorous triamide or an alkyl phosphoramide anionic compound to provide a dialkoxy alkylidene alkyne, and then either (1) hydrolyzing the dialkoxy alkylidene alkyne to form a novel aldehyde, an alkylidene alkynal, and if desired, reducing the triple bond of the alkylidene alkynal to a double bond to obtain the corresponding alkylidene alkenal or (2) first reducing the dialkoxy alkylidene alkyne to form a 1,1-dialkoxy-2-alkylidene-3-alkene and if desired then hydrolyzing said 1,1-dialkoxy-2-alkylidene-3-alkene to form the desired 2-alkylidene-3-alkenal; or (b) first reducing the alkynone to form a 1,1-dialkoxy-3-alken-2-one and then treating the 1,1-dialkoxy-3-alken-2-one with an alkylidene tri-substituted phosphorane or an alkylidene phosphorous triamide or an alkyl phosphoramide anionic compound to provide a dialkoxy alkylidene alkene and, if desired, then hydrolyzing said dialkoxy alkylidene alkene to form the desired 2-alkylidene-3-alkenal; together with novel alkylidene alkynals and acetals thereof so produced.

REFERENCES:
patent: 2855441 (1958-10-01), Sondheimer
patent: 3078256 (1963-02-01), Wittig et al.
patent: 3922309 (1975-11-01), Schreiber et al.
patent: 3970701 (1976-07-01), Sanderson et al.
patent: 4024190 (1977-05-01), Sanderson et al.

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