International Flavors & Fragrances Inc.

Robin L Kasper

Manfred H Vock

Braja D Mookherjee

Robert W Trenkle

Joaquin F Vinals

Frederick L Schmitt

Jacob Kiwala

John B Hall

Edward J Granda

Ronald Schreck

Described is a process for preparing .beta.-damascone starting with 2,6,6-trimethyl cyclohex-2-enone according to the reaction sequence: ##STR1## wherein Z is hydrogen, MgX', Li, Na or K; Y is MgX', Li, Na or K; X' is Cl, Br or I; R is C.sub.1 -C.sub.3 lower alkyl such as methyl, ethyl, n-propyl or i-propyl; X is Cl, Br or I. Also described are the organoleptic uses of the compound having the structure: ##STR2## in augmenting or enhancing the taste or aroma of a consumable material, e.g., foodstuff, chewing gum, medicinal product, chewing tobacco, smoking tobacco, perfume, perfumed article (e.g., drier-added fabric softener articles and solid or liquid anionic, cationic or nonionic detergents) and cologne.

Process for preparing acyl trimethyl cyclohexene derivatives and use of

Described is a process for augmenting or enhancing the aroma or taste of a smoking tobacco comprising the step of adding to smoking tobacco an organoleptic property modifying amount of the compound having the structure: ##STR1##

Use of acyl trimethyl cyclohexene derivatives in augmenting or enhancing

Described is the use of the compound having the structure: ##STR1## for augmenting or enhancing the aroma or taste of a foodstuff.

Use of 1-hydroxy-1-ethynyl-2,2,6-trimethyl cyclohexane in augmenting or

Described is a process for preparing .beta.-damascone starting with 2,6,6-trimethyl cyclohex-2-enone and its use in augmenting or enhancing the perfume and cologne.

Use of 1-acetyl-22,6-trimethyl cyclohexene-1 in augmenting or enhancing

Described is a process for augmenting or enhancing the aroma of a perfume composition as well as perfume and cologne compositions containing a mixture consisting essentially of compounds having the structures: ##STR1## and wherein the mixture contains 30% of the compounds having the structures; ##STR2## and 60% of the compound having the structure: ##STR3##

Perfume compositions containing 1-acyl-2,6,6-trimethylcyclohexene

A process is described for augmenting or enhancing the aroma or taste of a smoking tobacco comprising the step of adding to smoking tobacco a composition consisting essentially of an organoleptic modifying quantity of at least one 1-acetyl-2,2,6-trimethylcyclohexene having a structure selected from the group consisting of: ##STR1## also described are smoking tobacco articles comprising smoking tobacco and in intimate contact with said smoking tobacco a composition containing an organoleptic property modifying quantity of at least one 1-acetyl-2,6,6-cyclohexene derivative having a structure selected from the group consisting of: ##STR2##

Use in smoking tobacco compositions and smoking tobacco articles of

Described is a process for augmenting or enhancing the aroma of solid or liquid anionic, cationic or nonionic detergent compositions comprising adding to a solid or liquid anionic, cationic or nonionic detergent base, an aroma augmenting or enhancing quantity of at least one of the compounds having a structure: ##STR1## whereby sweet, floral, fruity, rose-like, minty/camphoraceous aromas with floral, hay-like, musty backgrounds and tobacco nuances are augmented, enhanced or imparted.

Detergent compositions containing 1-acyl-2,6,6-trimethylcyclohexene

Described is a process for augmenting or enhancing the aroma or taste of a foodstuff by adding to said foodstuff a mixture of compounds having the structures: ##STR1## wherein said mixture contains 30% of the compounds having the structures: ##STR2## and 60% of the compound having the structure: ##STR3##

Process for augmenting or enhancing the aroma or taste of a foodstuff by

Described are substituted 1-oxyalkyl-2,6,6-trimethylcyclohexene derivatives having the generic structure: ##STR1## wherein R.sub.1 is one of OH, ##STR2## OMgX or H; R.sub.2 is ##STR3## OH, OMgX, CH.sub.3, H; R.sub.3 is one of methyl, ethyl, 1-propyl or 2-propyl; X is chloro, bromo or iodo; R.sub.6 is hydrogen or no moiety; one of the wavy lines is a carbon-carbon double and the other of the wavy lines is a carbon-carbon single bond; with the first proviso that when the .DELTA..sup.2,3 bond is a carbon-carbon double bond, then R.sub.6 is hydrogen and the moieties R.sub.6 and ##STR4## are so juxtaposed as to give rise to two different groups of stereoisomers of the molecular genus: ##STR5## and with the second proviso that when R.sub.1 is one of ##STR6## OH or OMgX then R.sub.2 is hydrogen or methyl; and when R.sub.2 is one of ##STR7## OH or OMgX then R.sub.1 is hydrogen. Also described are processes for preparing such 1-oxyalkyl-2,6,6-trimethyl cyclohexene derivatives and organoleptic uses of such 1-oxyalkyl-2,6,6-trimethyl cyclohexene derivatives, with the exception of compounds wherein one of R.sub.1 or R.sub.2 is OMgX.

Substituted 1-oxyalkyl-2,6,6-trimethyl-cyclohexene derivatives,

Process intermediates are described herein having the generic structure: ##STR1## wherein X is selected from the group consisting of chloro, bromo and iodo; R.sub.3 is hydrogen or does not represent any group; wherein one of the wavy lines is a carbon-carbon double bond and the other of the wavy lines is a carbon-carbon single bond; with the proviso that when the .DELTA..sup.2,3 bond is a carbon-carbon double bond, then R.sub.3 is hydrogen and R.sub.3 and the moiety: ##STR2## are so juxtaposed that the molecule having the structure: ##STR3## exists in two different isomeric forms; a '+' form and '-' form.

1-Acyl-2,6,6-trimethylcyclohexene derivatives, processes for producing

Described is a process for preparing several 1-acyl-2,6,6-trimethylcyclohexene derivatives defined by the generic structure: ##STR1## wherein R.sub.1 is hydrogen or ethylidene having the structure:

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Eatontown, NJ, United States of America

Robin L Kasper