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US 5,965,767 AGranted
Beta ketoester compositions and method of manufacture
AssigneeThe Procter & Gamble Company
InventorsMark Robert Sivik, Frederick Anthony Hartman
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Abstract
A method for making beta ketoesters of alcoholic actives, especially perfume alcohols, by a two step process involving a first diketene reaction step and a second carboxylic acid halide reaction step. The present invention also relates to mixtures of beta ketoesters of such alcoholic actives, especially those prepared by the present manufacturing process.
Claims15
A method for manufacturing .beta.-ketoester compounds having the formula:
- ##STR5## said method comprising the steps of:
- (a) reacting one or more alcoholic actives having the formula R--OH, wherein R comprises from 5 to 30 carbon atoms, with a diketene having the formula:
- ##STR6## to produce a .beta.-ketoester having formula:
- ##STR7## wherein each R' is independently selected from the group consisting of hydrogen and C.sub.1 -C.sub.30 linear, branched, substituted or unsubstituted alkyl, alkenyl, and aryl;
- and
- (b) reacting said .beta.-ketoester from step (a) with one or more carboxylic acid halides having the formula:
- B--C(O)--X
- wherein B is selected from C.sub.1 -C.sub.30 alkyl, alkenyl, and aryl, linear or branched, substituted or unsubstituted, and X is selected from chloride, bromide, and mixtures thereof, to produce a .beta.-ketoester.
5 more elements
A method for manufacturing .beta.-ketoester compounds having the formula:
- said method comprising the steps of:
- (a) reacting an alcohol selected from the group consisting of linalool, tetrahydro-linalool, myrcenol, dihydromyrcenol, and mixtures thereof, with a diketene having the formula:
- ##STR11## to produce a ,ketoester having formula:
- ##STR12## wherein the unit --OR is derived from said alcohol, each R' is independently selected from the group consisting of hydrogen and C.sub.1 -C.sub.30 linear, branched, substituted or unsubstituted alkyl, alkenyl, and aryl;
- and
- (b) reacting said .beta.-ketoester from step (a) with one or more carboxylic acid halides having the formula:
- B--C(O)--X
- wherein B is selected from 1'-naphthyl, 2'-naphthyl, 4'-methoxyphenyl, 4'-nitrophenyl, octyl, and mixtures thereof;
- and X is selected from chloride, bromide, and mixtures thereof, to produce .beta.-ketoester.
6 more elements
A method for manufacturing ,ketoester compounds having the formula:
- ##STR13## said method comprising the steps of:
- a) reacting linalool with a diketene having the formula:
- ##STR14## to produce a .beta.-ketoester having formula:
- ##STR15## and b) reacting said ,ketoester from step (a) with 2-naphthoyl chloride in the presence of calcium hydroxide to form 3,7-dimethyl-1,6-octadien-3-yl 3-(.beta.-naphthyl)-3-oxo-propionate.
1 more element
Dependencies are inferred from the claim text.