Scm Corporation

Millennium Specialty Chemicals, Inc.

Millenium Specialty Chemicals, Inc.

Bernard J Kane

Richard A Von Genk

Sean G Traynor

Mark B Erman

Joe W Snow

James O Bledsoe, Jr

Levy A Canova

Henri M Hoffmann

Karen E Irving

Linda M Hirschy

Gary P Sanders

Cyclic ethers or chloroketones useful as fragrance components or intermediates are made by reacting a saturated, tertiary terpene alcohol with hypochloric acid under conditions effective to promote oxidation. trans-Pinanol gives predominantly 6,9-dimethyl-7-oxatricyclo[4.3.0.0]-nonane, while cis-pinanol yields almost exclusively 1-acetyl-3-(2-chloroethyl)-2,2-dimethylcyclobutane, a new and versatile intermediate for making cyclobutane derivatives having interesting and diverse aromas.

Fragrance compositions from tertiary terpene alcohols

Process for obtaining alpha-campholenic aldehyde

This invention relates to a compound having the formula I: ##STR1## wherein n is an integer of from 0 to 1; when n is 1, one of dashed lines a and b is a single bond and the other of dashed lines a and b is a double bond, dashed line c is not present, and dashed line d is a single bond; when n is 0, dashed lines a, b, c and d are single bonds or one of dashed lines a and b is a single bond and the other of dashed lines a and b is a double bond, dashed line c is not present, and dashed line d is a double bond; R.sub.1, R.sub.2 and R.sub.3 are, independently, lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.6 ; and R.sub.4 is hydrogen, lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.5, or C(O)R.sub.5, wherein R.sub.5 is hydrogen or lower branched or straight chain alkyl, alkenyl or alkynyl of C.sub.1 -C.sub.4 ; wherein the sum of the carbon atoms in R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is less than or equal to eight carbon atoms. These compounds can be prepared by the cyclization of 1,1,3-trialkyl-1,6-heptadien-3-ols in the presence of an acid. The compounds of formula I are used as fragrance ingredients to confer, enhance, improve, or modify the aroma of a perfumery composition or an article.

Cycloheptenols and their derivatives, methods of making thereof, and

Disclosed are novel cyclic terpenoid amines which can be prepared by cyclizing the corresponding acyclic terpenoid amine.

Cyclic terpenoid amines, their preparation and uses

Alkali metal oxides of cis- and trans-2,6,6-trimethylbicyclo(3.1.1)-heptan-2-ol are surprisingly effective bases in organic reactions calling for the use of a strong base, especially those reactions wherein abstraction of a proton from attachment to a carbon atom is postulated to occur in the mechanism.

Alkoxides of 2-pinanol

Para-menth-1-ene-7-sulfonate salts are made by reacting .beta.-pinene with a bisulfite salt under free radical conditions.

Para-menth-1-ene-7-sulfonic acid and salts thereof

A process for allylic rearrangement, particularly terpenoid allylic rearrangement, utilizing certain acid forming metals to form an ester or alcoholate (alcohologen) of the allylic alcohol to be rearranged, isomerizing and cleaving the alcohologen in the presence of a transition metal compound catalyst and recovering the rearranged alcohol.

Allylic rearrangement process

Preparation of para-menth-1-ene-7-sulfonate salts and corresponding acids

The compound d-isomenthoxyacetic acid and various ester and amide derivatives are useful resolving agents and perfume ingredients.

d-Isomenthoxyacetic acid

Acyclic terpenoid onium salts are cyclized in an acidic aqueous solution at a temperature of at least about 80.degree. C.

Cyclic terpenoid onium salts, their preparation and uses

.beta.-Phellandrene is prepared by pyrolyzing a para-menth-1-ene-7-sulfonate salt.

Preparation of .beta.-phellandrene

In a process for hydrogenation, with elemental hydrogen gas in the presence of a hydrogenation catalyst, of a cyclic unsaturated compound having an hydroxyl group projecting from an asymmetric center of the ring and an olefinic carbon-to-carbon double bond which when saturated in the hydrogenation process creates an additional asymmetric center in the ring, the improvement for obtaining increased stereoselectivity by increasing the addition of said hydrogen to that side of the olefin bond on the same side of the compound molecule as said hydroxyl group, comprising: conducting said hydrogenation with a nickel hydrogenation catalyst that has a substantial fraction of its reactive surfaces inactivated. The invention is particularly applicable to the hydrogenation of d-trans-piperitol to d-isomenthol.

Growing community of inventors

Atlantic Beach, FL, United States of America

Bernard J Kane