Basf Aktiengesellschaft

Dieter Degner

Heinz Hannebaum

Hardo Siegel

Walter Gramlich

Werner Hoffmann

Ludwig Schuster

Eberhard Steckhan

Norbert Goetz

Albrecht Harreus

Bernd Wolf

Hans Theobald

Costin Rentzea

Dieter Hermeling

Jochen Wild

Michael Steiniger

Lothar Janitschke

Frank Thoemel

Wolfgang Lengsfeld

Hans J Pander

Manfred Barl

Hans Roos

Juergen Haufe

Karl H Grosse-Brinkhaus

Franz Lanzendoerfer

Bernd Potzolli

Heinz Hannebau

Benzene derivatives of the general formula ##STR1## where Hal is halogen, R.sup.1 is a hydrocarbon radical of 1 to 18 carbon atoms, R.sup.2 is hydrogen or alkyl of 1 to 6 carbon atoms and X is hydrogen or halogen, are prepared by a process in which a toluene derivative of the general formula ##STR2## is electrochemically oxidized in the presence of an acid of the formula R.sup.2 --COOH (III). Novel benzene derivatives of the general formula ##STR3## where R.sup.3 is hydrogen or an R.sup.2 --CO-- radical but R.sup.1 cannot be methyl if X is hydrogen, and of the general formula ##STR4## where R.sup.4 is a branched or cyclic alkyl radical of 3 to 12 carbon atoms, but R.sup.4 cannot be isopropyl if X is hydrogen. The compounds of formulas IV and VI are intermediates for crop protecting agents, e.g. pyrethroids.

Benzyl alcohols and their lower alkanecarboxylic acid esters

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

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

A process for the preparation of a tetralin derivative of the formula ##STR1## where X is a --CH.sub.2 --, --CH(OH)-- or --CO-- group, R.sup.1 is one of the groups --COCH.sub.3, --CH(OR.sup.3).sub.2 or --CHO, R.sup.2 is hydrogen or methyl and R.sup.3 is alkyl of 1 to 4 carbon atoms, by electrochemical oxidation of a compound of the formula ##STR2## where R.sup.4 is methyl or ethyl and X and R.sup.2 have the abovementioned meanings, and novel tetralin derivatives.

Preparation of tetralin derivatives, and novel tetralin derivatives

A simple process for preparing 1-(4-hydroxy-phenyl)-butan-3-one, a sought-after natural aromatic, in a pure form and in good yield from easily accessible starting materials, wherein a 4-tert-alkoxy-benzaldehyde is condensed, under alkaline conditions, to give a novel 1-(4-tert.-alkoxy-phenyl)-but-1-en-3-one, the latter is hydrogenated, during or after this condensation, to give a novel 1-(4-tert.-alkoxy-phenyl)-butan-3-one, and isobutene or 2-methyl-but-1(2)-ene is eliminated from this compound in the presence of a catalytic amount of an acid. The novel intermediates have the general formula ##STR1## where R is H or CH.sub.3 and the broken line may or may not be an additional carbon-carbon bond.

Preparation of 1-(4-hydroxy-phenyl)-butan-3-one and novel intermediates

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

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

Biscarbamates, including novel one, of the general formula ##STR1## where R is alkyl of 1 to 8 carbon atoms and X is a hydrocarbon radical of 2 to 60 carbon atoms in which one or more carbon atoms may be replaced by hetero atoms and which may contain halogen atoms or ester, carbonyl or nitrile groups are prepared by electrochemically oxidizing formamides of the general formula ##STR2## in the presence of an alkanol of the formula ROH and of an ionic halide.

Preparation of biscarbamates and novel biscarbamates

Preparation of aromatic carboxylic acid ortho-esters of the formula I ##STR1## where R is C.sub.1 -C.sub.4 -alkyl and R.sup.1 is H, halogen, alkyl, aryl, heteroaryl, alkoxy, aryloxy, acyl, acyloxy or CN, by electro-oxidizing benzene derivatives of the formula II ##STR2## where R.sup.2 is CH.sub.3 or CH(OR.sub.2), in the presence of an alcohol ROH, a halogenated triarylamine compound and a base, and novel ortho-trialkyl 4-tert-butoxybenzoates, where alkyl is of 1 to 4 carbon atoms. Ortho-trialkyl 4-tert-butoxybenzoates are scents and are also used to prepared p-hydroxybenzoic acid esters.

Preparation of benzoic acid ortho-esters and novel compounds of this type

Preparation of carbamic acid esters

p-Alkoxycyclohexylalkanols and their esters of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.7 -alkyl, in particular tert.-butyl, or is cyclohexyl, R.sup.2 is C.sub.1 -C.sub.3 -alkyl, in particular methyl or ethyl, and R.sup.3 is hydrogen, acetyl, propionyl or butyryl, and scent compositions containing these compounds I and processes for their preparation. The novel compounds have fine woody or sandalwood notes and can be used as scents and as components of scent compositions.

p-Alkoxycyclohexylalkanols and p-alkoxycyclohexylalkyl esters and their

Aromatic carboxylates are prepared by electrochemical oxidation of the corresponding methyl benzenes or benzaldehyde dialkyl acetals in the presence of an alkanol and of a halogenated triarylamine derivative.

Preparation of aromatic carboxylates

Phthalaldehyde acetals of the formula ##STR1## where R is alkyl, are prepared by a process in which the corresponding bis-(alkoxymethyl)-benzenes are electrochemically oxidized in the presence of an alkanol of the formula ROH.

Preparation of phthalaldehyde acetals

Benzaldehyde dialkyl acetals of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each alkyl, are prepared by electrochemical oxidation of an alkyltoluene of the formula ##STR2## by a process in which the electrolyte used contains from 60 to 90% by weight of an alkanol of the formula R.sup.2 OH, from 8.5 to 40% by weight of the alkyltoluene and from 0.01 to 1.5% by weight of an HO.sub.3 S-containing acid.

Preparation of benzaldehyde dialkyl acetals

2,5-Dialkoxy-2,5-dihydrofurans are prepared by a process in which 2,5-dihydrofuran is oxidized electrochemically in the presence of an alkanol.

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Dannstadt-Schauernheim, Germany

Dieter Degner