Synthesis of α,β-unsaturated carboxylic acids and esters

Claim 1

A method of preparing alpha beta-unsaturated carboxylic acid esters, said method comprising: reacting in a Polar Solvent a vinylmercuric halide compound of the formula: ##STR42## in the presence of a noble metal carbonylation promoter selected from the group consisting of reaction equivalent amounts of noble metal simple salts in combination with lithium chloride, catalytic amounts of noble metals, and noble metal halide simple salts with carbon monoxide and an alcohol of the formula R'OH to provide an alpha beta-unsaturated carboxylic acid ester of the formula: ##STR43## at a percentage of theoretical yield of at least 85 weight %, wherein R, Z, W and R' are hydrogen or organic moieties which are non-reactive in the carbonylation reaction which occurs between said carbon monoxide and said vinylmercuric halide, of preselected determination to represent the desired ester being synthesized, and X is a halide.

Claim 2

A method of preparing alpha beta-unsaturated carboxylic acid esters, said method comprising: reacting in a Polar Solvent a vinylmercuric halide compound of the formula: ##STR42## in the presence of a noble metal carbonylation promoter selected from the group consisting of reaction equivalent amounts of noble metal simple salts in combination with lithium chloride, catalytic amounts of noble metals, and noble metal halide simple salts with carbon monoxide and an alcohol of the formula R'OH to provide an alpha beta-unsaturated carboxylic acid ester of the formula: ##STR43## at a percentage of theoretical yield of at least 85 weight %, wherein R, Z, W and R' are hydrogen or organic moieties which are non-reactive in the carbonylation reaction which occurs between said carbon monoxide and said vinylmercuric halide, of preselected determination to represent the desired ester being synthesized, and X is a halide.

Claim 11

The method of making alpha beta-unsaturated carboxylic acids, said method comprising; reacting a vinylmercuric halide compound of the formula: ##STR44## with carbon monoxide in the presence of water and a water miscible polar organic solvent and a noble metal carbonylation promoter selected from the group consisting of reaction equivalent amounts of noble metal simple salts in combination with lithium chloride, catalytic amounts of noble metals, and noble metal halide simple salts, the amount of said water being from about 1% by weight to about 10% by weight of the total amount of solvent present, said reaction being conducted at 20° C. or lower, to provide an alpha beta-unsaturated carboxylic acid of the formula: ##STR45## wherein R, Z and W are hydrogen or organic moieties which are non-reactive in the carbonylation reaction which occurs between said carbon monoxide and said vinyl mercuric halide, of pre-selected determination to represent the desired acid being synthesized, and X is the halide.

Claim 12

The method of making alpha beta-unsaturated carboxylic acids, said method comprising; reacting a vinylmercuric halide compound of the formula: ##STR44## with carbon monoxide in the presence of water and a water miscible polar organic solvent and a noble metal carbonylation promoter selected from the group consisting of reaction equivalent amounts of noble metal simple salts in combination with lithium chloride, catalytic amounts of noble metals, and noble metal halide simple salts, the amount of said water being from about 1% by weight to about 10% by weight of the total amount of solvent present, said reaction being conducted at 20° C. or lower, to provide an alpha beta-unsaturated carboxylic acid of the formula: ##STR45## wherein R, Z and W are hydrogen or organic moieties which are non-reactive in the carbonylation reaction which occurs between said carbon monoxide and said vinyl mercuric halide, of pre-selected determination to represent the desired acid being synthesized, and X is the halide.

Claim 16

A method of preparing alpha beta-unsaturated carboxylic acid esters, said method comprising: reacting in a Polar Solvent a vinylmercuric halide compound of the formula: ##STR46## in the presence of a noble metal carbonylation promoter selected from the group consisting of reaction equivalent amounts of noble metal simple salts in combination with lithium chloride, catalytic amounts of noble metals, and noble metal halide simple salts with carbon monoxide and an alcohol of the formula R'OH to provide an alpha beta-unsaturated carboxylic acid ester of the formula: ##STR47## wherein R, Z, W and R' are moieties which are non-reactive in the carbonylation reaction which occurs between said carbon monoxide and said vinylmercuric halide of preselected determination to represent the desired ester being synthesized, and X is a halide.

Claim 17

A method of preparing alpha beta-unsaturated carboxylic acid esters, said method comprising: reacting in a Polar Solvent a vinylmercuric halide compound of the formula: ##STR46## in the presence of a noble metal carbonylation promoter selected from the group consisting of reaction equivalent amounts of noble metal simple salts in combination with lithium chloride, catalytic amounts of noble metals, and noble metal halide simple salts with carbon monoxide and an alcohol of the formula R'OH to provide an alpha beta-unsaturated carboxylic acid ester of the formula: ##STR47## wherein R, Z, W and R' are moieties which are non-reactive in the carbonylation reaction which occurs between said carbon monoxide and said vinylmercuric halide of preselected determination to represent the desired ester being synthesized, and X is a halide.