Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1976-03-08
1977-08-30
Mars, Howard T.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
C07C 4330, A61K 746
Patent
active
040454975
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, hydrolyzying 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: 2657219 (1953-10-01), Isler et al.
patent: 2855441 (1958-10-01), Sondheimer
patent: 3453317 (1969-07-01), Marbet et al.
Brandsma, Preparative Acetylenic Chemistry, Elsevier Publishing, New York 1971, pp. 68, 81-82.
Wittig et al. Ber 94, (1961), pp. 676-687.
Pittet Alan O.
Schreiber William L.
Haidt Harold
International Flavors & Fragrances Inc.
Liberman Arthur L.
Mars Howard T.
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