The present invention relates to 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde and derivatives thereof, to a process for preparing said compounds, to the use of 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof or of mixtures of said compounds or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use of 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof for modifying the scent character of a fragranced composition; to compositions containing 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof or a mixture of said compounds or a stereoisomer thereof or a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition, comprising incorporating 2-(2,4,5-trimethylcyclohex-2-en-1-yl)-acetaldehyde or a specific derivative thereof or a mixture of said compounds or a stereoisomer thereof or a mixture of two or more stereoisomers thereof into said composition.

The present invention relates to 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde and derivatives thereof, to a process for preparing said compounds, to the use of 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof or of mixtures of said compounds or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use of 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof for modifying the scent character of a fragranced composition; to compositions containing 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde or a specific derivative thereof or a mixture of said compounds or a stereoisomer thereof or a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition, comprising incorporating 2-(2,4,5-trimethylcyclohex-2-en-1-yl)-acetaldehyde or a specific derivative thereof or a mixture of said compounds or a stereoisomer thereof or a mixture of two or more stereoisomers thereof into said composition.

The present invention concerns new stable compositions of 1-Z-bromoalk-1-ene compounds of general formula (A). These compositions are characterized in that they also comprise either at least one cyclic ether compound comprising between 4 and 6 carbon atoms, or at least one ether of general formula (B) in which R.sub.1 and R.sub.2 are identical or different and selected from the group consisting of: a linear or branched alkyl group containing 1 to 8 carbon atoms.

The present invention concerns new stable compositions of 1-Z-bromoalk-1-ene compounds of general formula (A). These compositions are characterized in that they also comprise either at least one cyclic ether compound comprising between 4 and 6 carbon atoms, or at least one ether of general formula (B) in which R.sub.1 and R.sub.2 are identical or different and selected from the group consisting of: a linear or branched alkyl group containing 1 to 8 carbon atoms.

The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCHO (2), wherein R.sup.3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCH(OR.sup.1)(OR.sup.2) (1), wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms; and R.sup.3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).

The present invention provide for preparing a formylalkenyl alkoxymethyl ether compound of the following general formula (2): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCHO (2), wherein R.sup.3 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and “a” represents an integer of 1 to 10, the process comprising: hydrolyzing a dialkoxyalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.3CH.sub.2OCH.sub.2O(CH.sub.2).sub.aCH═CHCH(OR.sup.1)(OR.sup.2) (1), wherein R.sup.1 and R.sup.2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R.sup.1 and R.sup.2 may form together a divalent hydrocarbon group, R.sup.1-R.sup.2, having 2 to 10 carbon atoms; and R.sup.3 and “a” are as defined above, in the presence of an acid while removing an alcohol compound thus generated to form the formylalkenyl alkoxymethyl ether compound (2).

The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aX.sup.1 (1) wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X.sup.1 represents a halogen atom, and “a” represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH.sub.2═CHCH═CH(CH.sub.2).sub.aOAc (5) wherein “a” is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH.sub.2═CHCH═CH(CH.sub.2).sub.aOH (6) wherein “a” is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

The present invention relates to a haloalkenyl alkoxymethyl ether compound of the following general formula (1): R.sup.1CH.sub.2OCH.sub.2OCH.sub.2CH.sub.2CH═CH(CH.sub.2).sub.aX.sup.1 (1) wherein R.sup.1 represents a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group, X.sup.1 represents a halogen atom, and “a” represents an integer of 3 to 14. The present invention also relates to processes for preparing a terminal conjugated alkadien-1-yl acetate compound of the following general formula (5): CH.sub.2═CHCH═CH(CH.sub.2).sub.aOAc (5) wherein “a” is as defined above, and Ac represents an acetyl group, and a terminal conjugated alkadien-1-ol compound of the following general formula (6): CH.sub.2═CHCH═CH(CH.sub.2).sub.aOH (6) wherein “a” is as defined above, from the haloalkenyl alkoxymethyl ether compound (1).

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH.sub.2CH.sub.2CH═CHCH.sub.2CH.sub.2OCH.sub.2OCH.sub.2R′ (1), R.sup.1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH.sub.3(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.8CH═CHCH.sub.2CH.sub.2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).

The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH.sub.2CH.sub.2CH═CHCH.sub.2CH.sub.2OCH.sub.2OCH.sub.2R′ (1), R.sup.1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH.sub.3(CH.sub.2).sub.3CH═CH(CH.sub.2).sub.8CH═CHCH.sub.2CH.sub.2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).