Basf Aktiengesellschaft

Frank Thoemel

Werner Hoffmann

Dieter Degner

Rudolf Kropp

Paul Naegele

Axel Nuerrenbach

Kurt Schneider

Hartwig Fuchs

Karl Seib

Werner Hoffman

Franz Wenisch

An improved process for the preparation of primary terpenoid alcohols, e.g. 6,7-dihydrogeraniol and phytol, and of their esters with formic acid. The terpenoid formates are obtained very advantageously by reacting the corresponding tert.-vinylcarbinols with more than 2 moles, per mole of vinylcarbinol, of aqueous formic acid of more than 70 percent strength by weight, or with anhydrous formic acid, at from 5.degree. to 100.degree. C. The primary terpenoid alcohols themselves are obtained from their formates by trans-esterification with a low-boiling alcohol in the presence of a catalytic amount of a strong base. The products are valuable compounds. For example, 6,7-dihydrogeraniol is used as a scent and phytol is used as a perfume fixative and as a starting material for the synthesis of naturally occurring materials.

Preparation of terpenoid formates

Trimethyl-p-benzoquinone of the formula I ##STR1## is prepared by a process wherein A. 2,5,6-trimethylcyclohex-2-en-1-one or 2,3,6-trimethylcyclohex-2-en-1-one is reacted with air or oxygen at from 0.degree. to 150.degree. C. in a virtually anhydrous low molecular weight alkanol in the presence of a catalytic amount of copper(I) oxide or copper(II) oxide and in the presence of from 1 to 10 moles of a hydrogen halide gas per mole of trimethylcyclohexenone, and thereafter

Preparation of 2,3,5-trimethyl-p-benzoquinone

Cyclopentadecanolide of the formula I ##STR1## is prepared by a process wherein 12-oxocyclopentadecanolide of the formula ##STR2## is reduced electrochemically.

Preparation of cyclopentadecanolide

A process for the preparation of resorcinol derivatives of the general formula I ##STR1## where R.sup.1 is carbalkoxy, nitrile, alkyl or H and R.sup.2 to R.sup.5 are H or lower alkyl, by reacting the corresponding cyclohexane-1,3-dione (II) with oxygen or an oxygen-containing gas in the presence of a catalytic amount of a copper compound and of from 1 to 10 moles of a hydrogen halide, or from 0.5 to 5 moles of thionyl chloride per mole of II, in an alkanol having from 1 to 6 carbon atoms, tetrahydrofuran or methyl tert.-butyl ether as the solvent, at from 0.degree. to 150 C., without the addition of a significant amount of water to the reaction mixture. Some of the resorcinol derivatives prepared are useful scents with fragrance notes of the character of the odoriferous substance of natural oak moss.

Preparation of resorcinol derivatives

Compounds of the formula I ##STR1## where R is a polyethylene glycol radical of 3 to 60 chain members or a polypropylene glycol radical of 3 to 60 chain members or the radical of an ethylene oxide/propylene oxide block polymer of average molecular weight from 300 to 8,500, and R' is straight-chain or branched alkyl of 1 to 10 carbon atoms, or benzyl.

Polyalkoxycarbinol cinnamates and protective sun agents containing these

2-(1-methyl-eth-1-en-1-yl)-,2-(1-methyl-prop-1-en-1-yl)-, 2-(eth-1-en-1-yl)- and 2-(prop-1-en-1-yl)-4-methyl-2,3-dihydro-6H-pyrans substituted in the 2-position of the side chain by hydroxymethyl, acyloxymethyl, alkoxycarbonylmethyl, halomethyl or formyl. The novel 4-methyl-2,3-dihydro-6H-pyrans are obtained by reaction of 3-methyl-but-3-en-1-ol with an appropriately substituted unsaturated aldehyde in the presence of an acid catalyst. The products possess very interesting organoleptic properties.

Novel 2,4-disubstituted pyran derivatives, their preparation and their

The preparation of bicyclic enol-ethers (I) ##STR1## (where n is from 3 to 12, and R.sup.1, R.sup.2 and R.sup.3 may be H or C.sub.1 --C.sub.4 -alkyl) by free radical adduct formation of CHR.sup.1 =CR.sup.2 --CHR.sup.3 --O--R.sup.4 (III)(where R.sup.4 is tert.-butyl, tetrahydrofuran-2-yl or tetrahydropyran-2-yl) with a cyclic ketone (IV) ##STR2## followed by acid-catalyzed cyclization, and novel compounds II ##STR3## The compounds (I) and (II) are intermediates for the synthesis of musk-like fragrances.

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Weinheim, Germany

Frank Thoemel