Iodine → 2-Propenoic acid, 3-phenyl-, methyl ester

Participants

Reaction Steps

On the other hand, it is known that the reaction of benzoyl chloride with methyl acrylate in the presence of stoichiometric amounts of a nickel(O) catalyst leads to the formation of methyl trans-3-benzoyl acrylate if the reaction mixture is subsequently treated with iodine in methanol. Methyl cinnamate is formed as a by-product in this reaction. Methyl cinnamate is obtained as the main product and methyl benzoyl acrylate as a by-product by reacting a complex formed from benzoyl-palladium chloride and triphenylphosphine with methyl acrylate at 70° to 85° C. in the presence of triethylamine. If only catalytic amounts of the palladium and the triphenylphosphine are employed, the equilibrium of the reaction is shifted in favour of the formation of methyl benzoyl acrylate (the ratio by weight of methyl benzoyl acrylate:methyl cinnamate is approx. 8.3:1) [cf. Transition Met. Chem. 2, 270 (1977) and 4, 298 (1979)]. Finally, it is known from Synthesis, 777 (1977), that the reaction of aromatic acid halides with 1-alkines, catalysed by Pd, leads to alkinyl ketones without decarbonylation.

Provenance & Evidence