Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1974-07-22
1976-01-06
Weinberger, Lorraine A.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
131 17, 131144, 252 89, 252132, 252522, 426534, C07C 5702
Patent
active
039313069
ABSTRACT:
A method for producing mixtures containing greater than 50% cis 2-methyl-3-pentenoic acid comprising first reacting methyl acetylene with a methyl magnesium halide to form a methylacetylene magnesium halide Grignard reagent; then reacting the methyl acetylene magnesium halide Grignard reagent with acetaldehyde to form a 3-pentyn-2-ol magnesium halide salt; then hydrolyzing the magnesium halide salt to form 3-pentyn-2-ol; then halogenating the 3-pentyn-2-ol to form a 4-halo-2-pentyne; then reacting magnesium with the 4-halo-2-pentyne to produce a 4-magnesium halo-2-pentyne Grignard reagent; then reacting the 4-magnesium halo-2-pentyne Grignard reagent with carbon dioxide to form a magnesium halo-carboxylate salt mixture of compounds having the structures: ##EQU1## (wherein X is halogen); then hydrolyzing the magnesium halo-carboxylate salt mixture to form a mixture of carboxylic acids having the structures: ##EQU2## then hydrogenating the aforementioned mixture of carboxylic acids to form a mixture containing 80% cis-2-methyl-3-pentenoic acid and 20% of 2-methyl-2-pentenoic acid.
REFERENCES:
mcGreer et al., Can. J. Chem., 41, 726-731 (1963).
Hall John B.
Shuster Edward J.
Vinals Joaquin
Vock Manfred Hugo
Haidt, Esq. Harold
International Flavors & Fragrances Inc.
Liberman, Esq. Arthur L.
Myers Jane S.
Weinberger Lorraine A.
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