Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1977-05-26
1978-08-15
Mars, Howard T.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260601R, 260594, 252522, 131144, 426533, 426534, 426650, C07C 4330, A61K 746
Patent
active
041072170
ABSTRACT:
Described are intermediates, acetals formed in processes for producing novel 2-alkylidene-3-alkynals and 2-alkylidene-3-alkenals which processes 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.
REFERENCES:
patent: 3922309 (1975-11-01), Schreiber et al.
patent: 3988487 (1976-10-01), Sanderson et al.
Pasternak et al., Bull. Soc. Chem. France, 1966, pp. 356-361.
Pittet Alan O.
Schreiber William L.
Haidt Harold
International Flavors & Fragrances Inc.
Liberman Arthur L.
Mars Howard T.
Wolffe Franklin D.
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