Process for preparing functional group-containing olefinic compounds
Assignee3M Innovative Properties Company
InventorsMarkus A. Wicki, Kent E. Nielsen
Life of this patent
Estimating the term…
Abstract
A process for preparing functional group-containing olefinic compounds comprises the steps of (a) reacting at least one alkylidene phosphorane with at least one carbonyl-containing compound that comprises at least one group that is a leaving group, or that is capable of subsequent conversion to a leaving group, to form an olefinic compound that comprises at least one leaving group, the carbonyl-containing compound being selected from the group consisting of ketones and aldehydes; and (b) reacting the olefinic compound with at least one functional group-containing nucleophile to form a functional group-containing olefinic compound.
Claims47
A process for preparing functional group-containing olefinic compounds comprising the steps of:
- (a) reacting (1) at least one alkylidene phosphorane comprising an alkylidene moiety and three other moieties bonded to its phosphorus atom, said alkylidene moiety optionally comprising one or more carbon to carbon double or triple bonds, with (2) at least one carbonyl-containing compound that comprises at least one group that is a leaving group, or that is capable of subsequent conversion to a leaving group, and that optionally comprises one or more isolated carbon to carbon double or triple bonds, to form an olefinic compound that comprises at least one leaving group, said carbonyl-containing compound being selected from the group consisting of ketones and aldehydes;
- and
- (b) reacting said olefinic compound with at least one functional group-containing nucleophile to form the corresponding functional group-containing olefinic compound.
A process for preparing pheromone compounds comprising the steps of:
- (a) reacting (1) a phosphorane compound selected from those represented by the following general formula:
- wherein:
- R1 is selected from the group consisting of hydrogen, alkyl groups, alkenyl groups, and alkynyl groups;
- and
- each R2 is independently selected from the group consisting of aryl groups and hetaryl groups;
- with (2) an aldehyde selected from those represented by the following general formula:
- wherein:
- X is a leaving group;
- and R3 is selected from the group consisting of alkylene, alkenylene, and alkynylene;
- to form an olefinic compound represented by the following general formula:
- and
- (b) reacting said olefinic compound with at least one carboxylate, sulfoxide, nitrogen oxide, or hydroxide to form the corresponding olefinic acetate, olefinic alcohol, olefinic aldehyde, or olefinic ketone.
A process for preparing pheromone compounds comprising the steps of:
- (a) reacting (1) a phosphorane compound selected from those represented by the following general formula:
- wherein:
- R1 is selected from the group consisting of hydrogen, alkyl groups, alkenyl groups, and alkynyl groups;
- and each R2 is independently selected from the group consisting of alkyl groups and cycloalkyl groups;
- with (2) an aldehyde selected from those represented by the following general formula:
- wherein:
- X is a leaving group;
- R3 is selected from the group consisting of alkylene, alkenylene, and alkynylene;
- to form an olefinic compound represented by the following general formula:
- and
- (b) reacting said olefinic compound with at least one carboxylate, sulfoxide, nitrogen oxide, or hydroxide to form the corresponding olefinic acetate, olefinic alcohol, olefinic aldehyde, or olefinic ketone.
A process for preparing functional group-containing olefinic compounds comprising the steps of:
- (a) reacting (1) at least one functional group-containing nucleophile with (2) at least one carbonyl-containing compound that comprises at least one group that is a leaving group, or that is capable of subsequent conversion to a leaving group, and that optionally comprises one or more isolated carbon to carbon double or triple bonds, to form the corresponding functional group-containing carbonyl-containing compound, said carbonyl-containing compound being selected from the group consisting of ketones and aldehydes;
- and
- (b) reacting said functional group-containing carbonyl-containing compound with at least one alkylidene phosphorane comprising an alkylidene moiety and three other moieties bonded to its phosphorus atom, said alkylidene moiety optionally comprising one or more carbon to carbon double or triple bonds, to form a functional group-containing olefinic compound.
A process for preparing 8-dodecenyl acetate comprising the steps of:
- (a) reacting butylidenetriphenylphosphorane with 8-bromooctan-1-al to form 8-dodecenyl bromide;
- and
- (b) reacting said 8-dodecenyl bromide with sodium acetate to form 8-dodecenyl acetate.
A process for preparing 11-tetradecenyl acetate comprising the steps of:
- (a) reacting propylidenetriphenylphosphorane with 11-bromoundecan-1-al to form 11-tetradecenyl bromide;
- and
- (b) reacting said 11-tetradecenyl bromide with sodium acetate to form 11-tetradecenyl acetate.
A process for preparing 8,10-dodecadienol comprising the steps of:
- (a) reacting butenylidenetri(n-butyl)phosphorane with 8-bromooctan-1-al to form 8,10-dodecadienyl bromide;
- (b) reacting said 8,10-dodecadienyl bromide with sodium acetate to form 8,10-dodecadienyl acetate;
- and
- (c) hydrolyzing said acetate to form 8,10-dodecadienol.
A process for preparing 8,10-dodecadienol comprising the steps of:
- (a) reacting butenylidenetri(n-butyl)phosphorane with 8-bromooctan-1-al to form 8,10-dodecadienyl bromide;
- (b) reacting said 8,10-dodecadienyl bromide with sodium hydroxide to form the 8,10-dodecadienol.
Dependencies are inferred from the claim text.