The regio-selective functionalization of a dialkyl benzene compound

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wherein the ratio of the compound functionalized at position (a) to the compound functionalized at the position (b) is at least 70:30, more particularly at least 80:20, still more particularly at least 85:15, and still more particularly at least 90:10, characterised in that the substituent R is an isobutyl group.

The present invention relates to novel compounds of general formulae (la), (lb) and (Ic) and to the stereoisomers thereof. The compounds are useful as a fragrance or as flavor as they have a sandalwood like scent. The invention also relates to a method for imparting or modifying a scent or a flavor to a composition by including said compounds into such composition, to a fragrance containing composition and/or a fragrance material containing said compound and to a process for preparing these compounds. X is C(R.sup.4)OH or CO; R.sup.1 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl and C.sub.3-C.sub.4-cycloalkyl, R.sup.2 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl and C.sub.3-C.sub.4-cycloalkyl, R.sup.3 is C.sub.1-C.sub.4-alkyl, R.sup.3a is selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl, R.sup.3b is hydrogen or together with R.sup.3a is CH.sub.2; R.sup.4 is selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl.

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The present invention relates to novel compounds of general formulae (la), (lb) and (Ic) and to the stereoisomers thereof. The compounds are useful as a fragrance or as flavor as they have a sandalwood like scent. The invention also relates to a method for imparting or modifying a scent or a flavor to a composition by including said compounds into such composition, to a fragrance containing composition and/or a fragrance material containing said compound and to a process for preparing these compounds. X is C(R.sup.4)OH or CO; R.sup.1 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl and C.sub.3-C.sub.4-cycloalkyl, R.sup.2 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl and C.sub.3-C.sub.4-cycloalkyl, R.sup.3 is C.sub.1-C.sub.4-alkyl, R.sup.3a is selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl, R.sup.3b is hydrogen or together with R.sup.3a is CH.sub.2; R.sup.4 is selected from the group consisting of hydrogen and C.sub.1-C.sub.4-alkyl.

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Provided herein are methods for producing cyclic and acyclic ketones from trimerization and dimerization of alkyl ketones, including for example methyl ketones. Such cyclic and acyclic ketones may be suitable for use as fuel and lubricant precursors, and may be hydrodeoxygenated to form their corresponding cycloalkanes and alkanes. Such cycloalkanes and alkanes may be suitable for use as fuels, including jet fuels, and lubricants.

Provided herein are methods for producing cyclic and acyclic ketones from trimerization and dimerization of alkyl ketones, including for example methyl ketones. Such cyclic and acyclic ketones may be suitable for use as fuel and lubricant precursors, and may be hydrodeoxygenated to form their corresponding cycloalkanes and alkanes. Such cycloalkanes and alkanes may be suitable for use as fuels, including jet fuels, and lubricants.

Provided herein are methods for producing cyclic and acyclic ketones from trimerization and dimerization of alkyl ketones, including for example methyl ketones. Such cyclic and acyclic ketones may be suitable for use as fuel and lubricant precursors, and may be hydrodeoxygenated to form their corresponding cycloalkanes and alkanes. Such cycloalkanes and alkanes may be suitable for use as fuels, including jet fuels, and lubricants.

A transfer-hydrogenation process for preparing a carbonyl compound and an alcohol compound comprises the steps of (a) contacting a first carbonyl compound with a first alcohol compound in the presence of a transfer-hydrogenation catalyst in a first reaction zone at conditions effective to form a second carbonyl compound from the first alcohol compound and a second alcohol compound from the first carbonyl compound, and (b) removing the second carbonyl compound from the first reaction zone during step (a). The first carbonyl compound is a saturated aldehyde or ketone, or an ,-unsaturated aldehyde or ketone. The first alcohol compound is a primary or secondary alcohol. The second alcohol compound is ,-saturated. The transfer-hydrogenation catalyst includes a Group 8 to 11 metal. This process is useful for preparing and higher value alcohols, such as butanol or 2-ethylhexanol, from the corresponding carbonyl compounds by engaging lower alcohol (C.sub.2-C.sub.4) feedstocks instead of hydrogen (H.sub.2).

A transfer-hydrogenation process for preparing a carbonyl compound and an alcohol compound comprises the steps of (a) contacting a first carbonyl compound with a first alcohol compound in the presence of a transfer-hydrogenation catalyst in a first reaction zone at conditions effective to form a second carbonyl compound from the first alcohol compound and a second alcohol compound from the first carbonyl compound, and (b) removing the second carbonyl compound from the first reaction zone during step (a). The first carbonyl compound is a saturated aldehyde or ketone, or an ,-unsaturated aldehyde or ketone. The first alcohol compound is a primary or secondary alcohol. The second alcohol compound is ,-saturated. The transfer-hydrogenation catalyst includes a Group 8 to 11 metal. This process is useful for preparing and higher value alcohols, such as butanol or 2-ethylhexanol, from the corresponding carbonyl compounds by engaging lower alcohol (C.sub.2-C.sub.4) feedstocks instead of hydrogen (H.sub.2).

Cyclohexenone and cyclohexenol compounds are provided having specific fragrances and remanence properties, along with methods for synthesizing these compounds, including obtaining the compound by condensing a ketone on an ?-methylene-aldehyde in order to obtain, by means of a domino reaction, compounds of formula (II) as follows: ##STR00001##

Cyclohexenone and cyclohexenol compounds are provided having specific fragrances and remanence properties, along with methods for synthesizing these compounds, including obtaining the compound by condensing a ketone on an ?-methylene-aldehyde in order to obtain, by means of a domino reaction, compounds of formula (II) as follows: ##STR00001##