Abstract: A process for making perillyl alcohol is disclosed. The process comprises isomerizing a starting material comprising trans-isocarveol at a temperature within the range of 100° C. to 220° C. in the presence of a Group 5 metal catalyst to produce perillyl alcohol. We surprisingly found that trans-isocarveol, which can be selectively produced from a commercially available mixture of cis- and trans-LMO, can be isomerized directly to perillyl alcohol. Yields of perillyl alcohol are improved when the isomerization is performed under an inert atmosphere and/or in the presence of a phenolic antioxidant. Performing the isomerization in the presence of a high-boiling alcohol and/or distilling the perillyl alcohol product from the reaction mixture in the presence of a high-boiling alcohol, enhances yields and maximizes catalyst use. The resulting distillation residue, which contains recovered Group 5 metal catalyst, is valuable for catalyzing additional trans-isocarveol isomerizations.

Abstract: A method of imparting a physiological cooling effect to a consumer product is disclosed. The method comprises formulating into the consumer product a composition comprising at least one lactoyl ester of menthyl lactate. Also disclosed is a method of providing physiological cooling by contacting skin or mucous membranes with the lactoyl ester compositions. Coolants comprising the lactoyl esters and additional coolants are also disclosed. The lactoyl esters are conveniently prepared from menthol and lactic acid.

Abstract: A process for separating at least one tertiary alcohol from at least one secondary alcohol from pine oil, the process comprising: reacting the pine oil comprising the at least one secondary alcohol and the at least one tertiary alcohol with at least one C3-C30 carboxylic acid ester, and at least one base, wherein the secondary alcohol is esterified to produce at least one secondary ester, with the proviso that the base is not a hydroxide; and separating the tertiary alcohol from the secondary ester.

Abstract: A process for preparing at least one alicyclic carboxylic acid compound by Grignard reaction, the process comprising: reacting magnesium and at least one alicyclic halide compound in at least one solvent to produce at least one alicyclic Grignard reagent; concurrently adding carbon dioxide to the magnesium, the alicyclic halide compound, the solvent, and the alicyclic Grignard reagent, while the alicyclic Grignard reagent is still being produced, to form at least one alicyclic carboxylate magnesium salt; and hydrolyzing the alicyclic carboxylate magnesium salt to form the alicyclic carboxylic acid compound; wherein the alicyclic Grignard reagent and the alicyclic carboxylate magnesium salt are prepared in a one-pot synthesis.

Abstract: A method for stabilizing menthyl lactate is disclosed. The method comprises combining water with a solution comprising menthyl lactate and a water-miscible organic solvent in amounts effective to precipitate menthyl lactate from the resulting aqueous mixture. The aqueous precipitation method is simple to practice, and it provides menthyl lactate having remarkably improved storage stability.

Abstract: A process for separating at least one tertiary alcohol from at least one secondary alcohol from pine oil, the process comprising: reacting the pine oil comprising the at least one secondary alcohol and the at least one tertiary alcohol with at least one organic carbonate, and at least one base, wherein the secondary alcohol is esterified to produce at least one secondary ester; and separating the tertiary alcohol from the secondary ester.

Abstract: 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[4.3.0.03,9]-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.

Abstract: A method for stabilizing menthyl lactate is disclosed. The method comprises combining water with a solution comprising menthyl lactate and a water-miscible organic solvent in amounts effective to precipitate menthyl lactate from the resulting aqueous mixture. The aqueous precipitation method is simple to practice, and it provides menthyl lactate having remarkably improved storage stability.

Abstract: A two-step aldol condensation process is disclosed. ?-Campholenic aldehyde (ACA) and methyl ethyl ketone (MEK) react in the presence of a base under conditions effective to produce a mixture comprising a high yield of ketol condensation products. Dehydration of the ketols in the presence of an organic sulfonic acid provides unsaturated ketones that are valuable intermediates for fragrance components for synthetic sandalwood products. Compared with the usual one-step, base-catalyzed approach, the two-step process increases the yield of all condensation products and maximizes production of the most valuable ketone isomers.

Abstract: A process for making monomenthyl esters of dicarboxylic acids is disclosed. Menthol reacts with a saturated, cyclic anhydride in the presence of a base catalyst under conditions effective to produce a mixture of mono- and bis-menthyl esters in which the molar ratio of mono- to bis-menthyl esters is enhanced compared with the ratio of esters produced in a similar uncatalyzed process.

Abstract: The present invention provides, in one aspect, a substantially pure ethyl ester of N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine. In another aspect, disclosed is a method for producing substantially pure ethyl ester of N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine. In still another aspect, disclosed are various consumer products comprising the substantially pure ethyl ester of N-[[5-methyl-2-(1-methylethyl)cyclohexyl]carbonyl]glycine disclosed herein.

Abstract: A simple, high-yield process for making menthyl lactate (ML) is disclosed. Menthol and lactic acid react to produce a mixture comprising menthyl lactate and one or more higher lactoyl esters of ML. Hydrolysis of the esterification mixture follows in the presence of aqueous base under conditions effective to convert the higher lactoyl esters to menthyl lactate. Coincidentally, the conditions minimize hydrolysis of menthyl lactate to menthol, thereby maximizing the overall yield of ML.

Abstract: A process for the manufacture of an alpha, beta-unsaturated cyclic ketone, such as carvone, comprises the dehydrogenation of a secondary allylic cyclic alcohol, such as carveol, in the presence of at least one metal carboxylate. The process can be performed in a batchwise or continuous mode. Examples of suitable metal carboxylates include magnesium stearate, calcium 2-ethylhexanoate, and zinc 2-ethylhexanoate.

Abstract: A catalyst system comprising a primary catalyst chosen from one or more homogeneous or heterogeneous, inorganic, organic or complex metal-containing compound; and one or more phenolic activator/modifier(s). The catalyst system can be used for the preparation of allylic alcohols by rearrangement of corresponding epoxides, the subsequent Oppenauer type oxidation of allylic alcohols to alpha, beta-unsaturated carbonyl compounds, and/or the preparation of alpha, beta-unsaturated carbonyl compounds by rearrangement of epoxides to corresponding allylic alcohols followed by the subsequent Oppenauer type oxidation of allylic alcohols in a one pot process.

Abstract: A process for obtaining an amide of the general formula R-(CO)—NH—CH2—X involves contacting a nitrile of the general formula R-CN with:

Abstract: A process for obtaining alpha-campholenic aldehyde, which is useful as an aroma chemical and as a synthetic intermediate for other aroma chemicals, particularly those with a sandalwood odor, and also for some pharmaceuticals, is provided. In particular, the invention includes a continuous process for obtaining optically active or racemic &agr;-campholenic aldehyde by a catalytic rearrangement of optically active or racemic &agr;-pinene oxide that can be commercially practicable. In one embodiment, the method comprises continuously feeding &agr;-pinene oxide to a mixture including catalyst(s) and solvent(s), where the solvent(s) have a boiling point higher than the boiling point of &agr;-campholenic aldehyde, under conditions sufficient to provide for the complete, or at least partial, conversion of &agr;-pinene oxide into &agr;-campholenic aldehyde. The process further includes continuously removing &agr;-campholenic aldehyde from the reaction zone by suitable techniques such as distillation.

Abstract: A process for obtaining an amide of the general formula R—(CO)—NH—CH2—X involves contacting a nitrile of the general formula R—CN with: a) an acid; and c) an alkoxy-containing compound comprising at least one alkoxy functionality of the general formula —OCH2—X; wherein R is hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, which substituents can be substituted or unsubstituted; wherein X is hydrogen or a radical having the general formula —CHR1R2; and wherein R1 and R2 independently or collectively represent hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, or heterocyclic substituent, or any combination thereof, which substituents can be substituted or unsubstituted.

Abstract: Acid catalyzed cyclization of Diels-Alder adducts of myrcene is performed in the presence of hydroxyl-containing compounds, giving the resulting mixtures of isomeric acyloctahydronaphthalenes enhanced quantities of isomers that are particularly useful in perfumery because of their woody-amber odors with enhanced amber note.

Abstract: A process for obtaining a nitrile represented by formula RCN, comprising contacting a corresponding aldehyde represented by formula RCHO with (i) ammonia or ammonium hydroxide, and (ii) hydrogen peroxide, in the presence of a transition metal or a transition metal compound.