Process for producing ester compound having an internal unsaturated bond or cyclic olefin

A process for producing an unsaturated bond-containing ester compound, comprising:

• reacting an internal olefin or a cyclic olefin having one carbon-carbon double bond or more at a position other than terminals of a molecule thereof (the internal olefin and the cyclic olefin may each contain a hetero atom) with a carboxylic acid having a carboxylic group in an amide-based solvent in the presence of a palladium catalyst, a base, and molecular oxygen, to thereby obtain an ester compound having an unsaturated bond,
• wherein
• the amide-based solvent is represented by the following formula (1):
• wherein the formula (1), R1 represents an alkyl group having 1 to 4 carbon atoms;
• R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group;
• and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure;
• the internal olefin or the cyclic olefin is a compound represented by the following formula (2):
• wherein the formula (2), R4 to R7 each independently represent one selected from the group consisting of a hydrogen atom, alkyl groups, alkenyl groups, and aryl groups;
• the alkyl group, the alkenyl group, and the aryl group may each contain a hetero atom,
• at least one of R4 and R5 is any one of alkyl groups, alkenyl groups, and aryl groups,
• at least one of R6 and R7 is any one of alkyl groups, alkenyl groups, and aryl groups;
• when R4 and R6 are each an alkyl group or an alkenyl group,
• R4 and R6 may be bonded to each other to form a ring structure, and
• when R5 and R7 are each an alkyl group or an alkenyl group, R5 and R7 may be bonded to each other to form a ring structure;
• the ester compound is represented by the following formula (3):
• wherein the formula (3), R8 to R13 each independently represent one selected from the group consisting of a hydrogen atom, alkyl groups, alkenyl groups, and aryl groups;
• the alkyl group, the alkenyl group, and the aryl group may each contain a hetero atom;
• at least one of R8 to R11 is any one of alkyl groups, alkenyl groups, and aryl groups;
• when R8 and R12 are each an alkyl group or an alkenyl group, R8 and R12 may be bonded to each other to form a ring structure;
• and when R9 and R10 or R11 are each an alkyl group or an alkenyl group, R9 and R10 or R11 may be bonded to each other to form a ring structure;
• the palladium catalyst is a palladium halide;
• and
• the ester compound is formed by bonding an oxygen atom in the carboxyl group of the carboxylic acid to at least one of carbon atoms constituting the carbon-carbon double bond and carbon atoms at allylic positions of the internal olefin or the cyclic olefin.