International Flavors & Fragrances Inc.

Lambert Dekker

Richard M Boden

Frederick L Schmitt

Augustinus G Van Loveren

William L Schreiber

Futoshi Fujioka

Patrick Chant

Jacob Kiwala

Philip T Klemarczyk

Described are hydrocarbyloxy alkanals defined according to the generic structure: ##STR1## wherein R.sub.1 represents one of the moieties: ##STR2## and R.sub.2 represents hydrogen or methyl prepared according to the process of first reacting an allyl alcohol defined according to the structure: ##STR3## with a hydrocarbon or hydrocarbyl halide defined according to the structure: ##STR4## having an electrophilic center wherein R.sub.1 ' is saturated or unsaturated hydrocarbyl and X represents halogen or hydrogen with the provisos that:

Hydrocarbyloxy alkanals, organoleptic uses thereof and process for

Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene) and then oxidizing the resulting product using formic acid and hydrogen peroxide; and optionally reacting the resulting product with a methyl Grignard reagent such as methyl magnesium chloride followed by hydrolysis; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same. Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.1 and R.sub.2 taken together represent oxygen; or wherein, taken separately, R.sub.1 is hydroxyl and R.sub.2 is methyl or R.sub.1 is oxymagnesium halide and R.sub.2 is methyl; and wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl with the provisos that:

Methyl substituted-2-oxohexane derivatives and processes for preparing

Described are hydrocarbyloxy alkanals defined according to the generic structure: ##STR1## wherein R.sub.1 represents one of the moieties: ##STR2## and R.sub.2 represents hydrogen or methyl prepared according to the process of first reacting an allyl alcohol defined according to the structure: ##STR3## with a hydrocarbon or hydrocarbyl halide defined according to the structure:

Hydrocarbyloxy alkanal

Organoleptic uses of hydrocarbyloxy alkanals

Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene); then oxidizing the resulting product using formic acid and hydrogen peroxide; then reducing the resulting ketone(s) with an alkali metal borohydride; and then, optionally, reacting the resulting alcohol(s) with acetic anhydride to form one or more esters; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic cationic nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same. Also covered is the genus of compounds defined according to the structure: ##STR1## wherein R.sub.12 represents hydroxyl:

Processes for preparing methyl substituted-2-oxohexane mixtures

Described is a process for augmenting or enhancing the aroma or taste of smoking tobacco compositions and/or smoking tobacco article components comprising the step of adding to a smoking tobacco composition and/or smoking tobacco article component, an aroma or taste augmenting or enhancing quantity of at least one compound defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; wherein R.sub.4 represents methyl or ethyl; wherein one of R.sub.1, R.sub.2 and R.sub.3 represents 2-methyl-1-propenyl or 2-methyl-1-propylidenyl; and the other of R.sub.1, R.sub.2 and R.sub.3 represent hydrogen; with the provisos that:

Use of substituted methyl isopropyl cyclohexenones in augmenting or

Described is the genus of compounds defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; wherein R.sub.4 represents methyl or ethyl; wherein one of R.sub.1, R.sub.2 and R.sub.3 represents 2-methyl-1-propenyl or 2-methyl-1-propylidenyl; and the other of R.sub.1, R.sub.2 and R.sub.3 represent hydrogen; with the provisos that:

Substituted methyl isopropyl cyclohexenones, organoleptic uses thereof

Described are hydrocarbyloxy alkanals defined according to the generic structure: ##STR1## wherein R.sub.1 represents one of the moieties: ##STR2## and R.sub.2 represents hydrogen or methyl prepared according to the process of first reacting an allyl alcohol defined according to the structure: ##STR3## with a hydrocarbon or hydrocarbyl halide defined according to the structure

Norbornyl oxybutyraldehyde

Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel methyl substituted-2-oxohexane derivatives produced by dimerizing isoamylene (2-methyl-2-butene); then oxidizing the resulting product using formic acid and hydrogen peroxide; then reducing the resulting ketone(s) with an alkali metal borohydride; and then, optionally, reacting the resulting alcohol(s) with acetic anhydride to form one or more esters; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations, perfumed polymers and deodorant compositions as well as bleaching compositions containing same. Also covered is the genus of compounds defined according to the structure ##STR1## wherein R.sub.12 represents hydroxyl:

Methyl substituted-2-oxohexane derivatives and process for preparing and

Described is the genus of compounds defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; wherein R.sub.4 represents methyl or ethyl; wherein one of the R.sub.1, R.sub.2 and R.sub.3 represents 2-methyl-1-propenyl or 2-methyl-1-propylidenyl; and the other of R.sub.1, R.sub.2 and R.sub.3 represent hydrogen; with the provisos that:

Described are methods for augmenting or enhancing the aroma of perfumes and perfumed articles by adding thereto perfume aroma augmenting or enhancing quantities of novel C.sub.10 -branched olefin epoxide mixtures produced by dimerizing isoamylene, (2-methyl-2-butene) and then epoxidizing the resulting product; as well as perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations and deodorant compositions as well as bleaching compositions containing same.

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Wyckoff, NJ, United States of America

Lambert Dekker