Basf Aktiengesellschaft

Walter Gramlich

Hardo Siegel

Dieter Degner

Ludwig Schuster

Klaus Halbritter

Werner Hoffmann

Gerd Heilen

Wolfgang Lengsfeld

Ernst-Heinrich Pommer

Rainer Becker

Heinz Hannebaum

Gerald Lauterbach

Roland Martin

Eberhard Ammermann

Hubert Sauter

Norbert Goetz

Karl Eicken

Walter Himmele

Leopold Hupfer

Costin Rentzea

Stephan Hueffer

Volker Bach

Eckhard Hickmann

Guenter Scherr

Heinz Eckhardt

Christoph Martin

Hermann Graf

Juergen Paetsch

Bernd Meissner

Michael Huellmann

Oliver Reese

Stefan Schroeder

Hans-Ulrich Scholz

Klaas Jansen

Walter Best

Gerhard Schindler

Werner Hoffman

Franz Lanzendoerfer

Frank F Pape

Adducts are obtained by reacting carbonyl compounds of the formula I where Rand Rare as defined, with cyclic compounds of the formula II where X is selected from oxygen, sulfur and N&#x2014;R, R-Rare as defined, and n is an integer from 1 to 4, which adducts are useful as tanning agents and preservatives.

Adducts based on cyclic compounds and the use thereof as tanning agents and curing agents

Preparation of vinyl glycols (I) ##STR1## (R.sup.1 to R.sup.6 =H, a carbo-organic radical, optionally substituted) in which an unsaturated diol of formula II ##STR2## is isomerized in the presence of a rhenium catalyst under neutral conditions. The compounds (I) serve as intermediates for the preparation of active substances and for the preparation of polymers.

Preparation of vinyl glycols

Cyclopentanones monoalkylated in the 2-position and of the general formula I ##STR1## where R.sup.1 is a branched or straight-chain aliphatic group of 2 to 12 carbon atoms and R.sup.2 to R.sup.7 may be identical or different and are each hydrogen or alkyl of 1 to 5 carbon atoms, are prepared by a process in which a cyclopentanone of the general formula II ##STR2## or a corresponding cyclopentenone, is reacted with an aldehyde of the general formula III ##STR3## at from 80.degree. to 280.degree. C. in the presence of hydrogen in an autoclave, over a catalyst which contains, as active components, on the one hand an oxide or a phosphate of magnesium, aluminum, titanium or zinc or of one of the rare earth metals, and on the other hand a noble metal of group VIII of the periodic table, preferably palladium. The 2-alkylcyclopentanones obtainable according to the invention in a simple single-stage reaction with virtually complete conversion and high selectivity are important as intermediates and in particular as scents.

Preparation of 2-alkylcyclopentanones

Alkyl-substituted cinnamaldehydes of the formula I ##STR1## where one or more of R.sup.1 , R.sup.2 and R.sup.3 is alkyl of from 1 to 8 carbon atoms, preferably of from 1 to 4 carbon atoms, and non-alkyl R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, which comprises heating acetylene alcohols of the general formula II ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each as defined above, in the presence of from 55 to 98% strength aqueous formic acid.

Preparation of alkyl-substituted cinnamaldehydes

3-tert-butyl-4-methoxycyclohexylmethanol, its preparation and its use as a scent.

3-tert-butyl-40-methoxycyclohexylmethanol, its preparation and its use

Alkylated dodecahydronaphtho[2,1-b]furans of the general formula I ##STR1## where R.sup.1 and R.sup.2 are identical and each is hydrogen or methyl are prepared by reacting alkylated 2-hydroxydecahydronaphthalene-1-ethanol of the formula II ##STR2## where R.sup.1 and R.sup.2 are as defined above, with a sulfonyl chloride in the presence of basic catalysts by performing the cyclization in the presence of concentrated aqueous alkali metal hydroxides and a phase transfer catalyst, preferably a tetra-substituted ammonium or phosphonium salt, the sulfonyl chloride used preferably comprising a sulfonyl chloride of the general formula III

Preparation of alkylated dodechydronaphto[2,1-b]furans

4-isopropylcyclohexylmethanol and its alkyl ethers of the general formula I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, are prepared by a process in which the novel 4-(1-alkoxy-1-methylethyl)-benzaldehyde or its dialkyl acetal of the general formula II ##STR2## where X is oxygen (IIa) or its two R.sup.2 O groups (IIb) and R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.4 -alkyl, is heated to 100.degree.-250.degree. C., preferably 130.degree.-200.degree. C., under a hydrogen pressure of from 50 to 350, preferably from 150 to 300, bar in the presence of a noble metal of group VIII of the Periodic Table.

Prepartion of 4-isopropylcyclohexylmethanol and its alkyl ethers

4-methyl-4-phenyl-1-pentanals of the general formula I ##STR1## where R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sup.2 is hydrogen or methyl, with the exception of 4-methyl-4-phenyl-1-pentanal, and the use of the methylphenylpentanals of the formula I for imparting fragrance properties to, or improving or modifying the fragrance properties of, perfumes and perfumed products, and the preparation of these compounds by hydroformylation of the corresponding 3-methyl-3-phenyl-1-butenes of the general formula II ##STR2## and, if required, subsequent reaction with formaldehyde and partial hydrogenation.

4-Methyl-4-phenyl-1-pentanals, their preparation and their use as scents

.gamma.-butyrolactones of the general formula I ##STR1## where R.sup.1 is hydrogen or alkyl of 1 to 4 carbon atoms which may be substituted by lower alkoxy or acyloxy and R.sup.2 is hydrogen or straight-chain or branched alkyl which is unsubstituted or substituted by a functional group or is aryl, are prepared by reacting an alkylene oxide of the general formula II ##STR2## with an acylacetate of the general formla III ##STR3## where R.sup.1 and R.sup.2 have the above meanings and R.sup.3 and R.sup.4 are each alkyl of 1 to 6 carbon atoms or aryl, and R.sup.4 may furthermore be hydrogen, in the presence of a catalyst at elevated temperatures, by a process in which the reaction is carried out in the presence of an alkali metal halide, of an ammonium halide, preferably a quaternary ammonium halide, of a phosphonium halide, of an alkali metal phosphate or of an alkali metal carbonate at from 20.degree. to 200.degree. C. and under from 1 to 50 bar.

Preparation of alpha-substituted upsilon-butyrolactones

Benzaldehyde dialkyl acetals of the formula ##STR1## where R is alkyl of 1 to 4 carbon atoms, are prepared by electrochemical oxidation of 3-tert-butyl-4-methoxytoluene in the presence of an alkanol of the formula ROH and are used as scents or scent intermediates.

Novel benzaldehyde dialkyl acetals and preparation and use thereof

Benzaldehyde derivatives of the general formula I, where X is an oxygen atom or two R.sup.2 O groups and R.sup.1 and R.sup.2 are alkyl radicals of 1-4 carbon atoms, their preparation, and their use as odorants or odorant intermediates. ##STR1##

Novel benzaldehyde derivatives, their preparation, and their use

.beta.-Dicarbonyl and .beta.-cyanocarbonyl compounds ##STR1## where R.sup.1 is alkyl of 1-20 carbons, X is --COR.sup.2, Y is --COOR.sup.3, --COR.sup.3 or --CN, and R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.10 -alkyl, are prepared from R.sup.1 --CHO (II) and X--CH.sub.2 --Y (III) by reaction in the presence of a condensation catalyst, hydrogen and a hydrogenation catalyst, using an oxide or phosphate of Mg, Al, Ti, Zn or a rare earth metal as the condensation catalyst.

Preparation of .alpha.-substituted .beta.-dicarbonyl and

2-methyl-3-(p-methylphenyl)-propionitrile is prepared for use as a scent.

2-methyl-3-(p-methylphenyl)propionitrile, preparation and use thereof as

Substituted 4-methyl-4,7-dihydro-1,3-dioxepins of the general formula I ##STR1## where R.sup.1 is an alkyl of 1 to 12 carbon atoms which may furthermore contain oxygen in the form of an ether group, or a 5-membered to 8-membered ring which is unsubstituted or substituted by alkyl groups and/or an alkylene group, has up to 10 carbon atoms and may furthermore contain oxygen in the form of an ether group, and R.sup.2, R.sup.3 and R.sup.4 are each hydrogen or methyl, with the exception of the compound 2-tert-butyl-4,7-dihydro-4,7-dimethyl-1,3-dioxepin, the preparation of substituted 4-methyl-4,7-dihydro-1,3-dioxepins and their use as scents and aromas, and scent compositions containing these compounds.

Substituted 4-methyl-4,7-dihydro-1,3-dioxepins, their preparation and

Aliphatic aldehydes of the general formula I ##STR1## where R.sup.1 is hydrogen or methyl,

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Edingen-Neckarhausen, Germany

Walter Gramlich