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US 4,070,374 AGranted
Process for the preparation of aryl substituted aldehydes, ketones and alcohols
AssigneeGivaudan SA
InventorsAlan J. Chalk, Steven A. Magennis
Life of this patent
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Abstract
Upon reacting an alcohol having an olefinic double bond with an aryl bromide or iodide in the presence of a Paladium catalyst, there is provided either an aryl substituted aldehyde, ketone or olefinic alcohol.
Claims18
A process for reacting an aryl compound of the formula:
- ##STR252## wherein R.sub.3 is (CH.sub.3).sub.3 C-- or (CH.sub.3).sub.2 CH--;
- with methallyl alcohol to provide a compound of the formula:
- ##STR253## wherein, an inert atmosphere is employed and there is used, a. 0.5 to 2.0 moles of methallyl alcohol per mole of aryl bromide;
- b. a palladium catalyst selected from the group consisting of PdCl.sub.2, PdCl.sub.2 (C.sub.6 H.sub.5 CN).sub.2, and (CH.sub.3 COO).sub.2 Pd in an amount equivalent, by weight, to 0.01 to 1.0% of the aryl bromide;
- c. one to two moles of sodium bicarbonate per mole of aryl bromide;
- d. from 0.01 to 1.0 moles of sodium iodide per mole of aryl bromide;
- and
- e. a solvent selected from the group consisting of hexamethylphosphoramide, dimethylacetamide, dimethylformamide, N-methylpyrrolidinone and tetramethylurea.
5 more elements
A process for reacting an aryl compound of the formula:
- ##STR256## wherein:
- R.sub.3 is hydrogen or, in combination with R.sub.4 represents --O--CH.sub.2 --O--;
- R.sub.4 is hydrogen or in combination with R.sub.3 represents --O--CH.sub.2 --O--;
- R.sub.5 is hydrogen or, when R.sub.3 and R.sub.4 are hydrogen, --CH.sub.3 ;
- with methallyl alcohol to provide a compound of the formula:
- ##STR257## wherein an inert atmosphere is employed and there is used, a. 0.5 to 2.0 moles of methallyl alcohol per mole of aryl bromide;
- b. a palladium catalyst selected from the group consisting of PdCl.sub.2, PdCl.sub.2 (C.sub.6 H.sub.5 CN).sub.2 and (CH.sub.3 COO).sub.2 Pd in an amount equivalent, by weight, to 0.01 to 1.0% of the aryl bromide;
- c. from 2 to 4 moles of triphenylphosphine per mole of palladium;
- d. from 1 to 2 moles of sodium bicarbonate per mole of aryl bromide;
- and
- e. a solvent selected from the group consisting of hexamethylphosphoramide, dimethylacetamide, dimethylformamide, N-methylpyrrolidinone and tetramethylurea.
8 more elements
A process for reacting bromobenzene with 2-methyl-3-buten-2-ol or 2-ethyl-3-buten-2-ol to provide a compound of the formula:
- ##STR262## wherein R.sub.9 is methyl or ethyl, an inert atmosphere is employed and there is used,
- a. 0.5 to 2.0 moles of the alcohol reactant per mole of bromobenzene;
- b. a palladium catalyst selected from the group consisting of PdCl.sub.2, PdCl.sub.2 (C.sub.6 H.sub.5 CN).sub.2 and (CH.sub.3 COO).sub.2 Pd in an amount equivalent, by weight, to 0.01 to 1.0% of bromobenzene;
- c. from two to four moles of triphenylphosphine per mole of palladium;
- d. from one to two moles of sodium bicarbonate per mole of bromobenzene;
- and
- e. from 0.01 to 0.5 moles of aliphatic tertiary amines per mole of bromobenzene;
- f. a solvent selected from the group consisting of hexamethylphosphoramide, dimethylacetamide, dimethylformamide, N-methylpyrrolidinone and tetramethylurea.
5 more elements
A process for reacting an aryl compound of the formula:
- ##STR265## wherein R.sub.3 is selected from the group consisting of H, OH and ##STR266## with methyl vinyl carbinol to provide a compound of the formula:
- ##STR267## wherein an inert atmosphere is employed and there is used a. 0.5 to 2.0 moles of methyl vinyl carbinol per mole of aryl bromide;
- b. a palladium catalyst selected from the group consisting of PdCl.sub.2, PdCl.sub.2 (C.sub.6 H.sub.5 CN).sub.2 and (CH.sub.3 COO).sub.2 Pd in an amount equivalent, by weight, to 0.01 to 1.0% of the aryl bromide;
- c. from 2 to 4 moles of triphenylphosphine per mole of palladium;
- d. from 1 to 2 moles of sodium bicarbonate per mole of aryl bromide;
- and
- e. a solvent selected from the group consisting of hexamethylphosphoramide, dimethylacetamide, dimethylformamide, N-methylpyrrolidinone and tetramethylurea.
4 more elements
A process for reacting bromobenzene with allyl alcohol to provide a mixture of 3-phenylpropanal and 2-phenylpropanal wherein an inert atmosphere is employed and there is used,
- a. 0.5 to 1.2 moles of allyl alcohol per mole of bromobenzene;
- b. a palladium catalyst selected from the group consisting of PdCl.sub.2, PdCl.sub.2 (C.sub.6 H.sub.5 CN).sub.2 and (CH.sub.3 COO).sub.2 Pd in an amount equivalent, by weight, to 0.01 to 1.0% of bromobenzene;
- c. from two to four moles of triphenylphosphine per mole of palladium;
- d. from one to two moles of sodium bicarbonate per mole of bromobenzene;
- and
- e. from 0.01 to 0.5 moles of an aliphatic tertiary amine per mole of bromobenzene;
- f. a solvent selected from the group consisting of hexamethylphosphoramide, dimethylacetamide, dimethylformamide, N-methylpyrrolidinone and tetramethylurea.
4 more elements
A process for reacting p-methoxybromobenzene with methallyl alcohol to provide a compound of the formula:
- ##STR272## wherein an inert atmosphere is employed and there is used, a. 0.5 to 2.0 moles of methallyl alcohol per mole of p-methoxybromobenzene;
- b. a palladium catalyst selected from the group consisting of PdCl.sub.2, PdCl.sub.2 (C.sub.6 H.sub.5 CN).sub.2, and (CH.sub.3 COO).sub.2 Pd in an amount equivalent, by weight, to 0.01 to 1.0% of the aryl bromide;
- c. 1 to 2 moles of sodium bicarbonate per mole of aryl bromide;
- d. from 2 to 4 moles of triphenylphosphine per mole of palladium;
- and
- e. a solvent selected from the group consisting of hexamethylphosphoramide, dimethylacetamide, dimethylformamide, N-methylpyrrolidinone and tetramethylurea.
3 more elements
Dependencies are inferred from the claim text.