Basf Aktiengesellschaft

Werner Hoffman

Karl Von Fraunberg

Rudolf Kropp

Axel Nuerrenbach

Manfred Baumann

Hartwig Fuchs

Norbert Mueller

Frank Thoemel

Franz Wenisch

A mixture of Z- and E-2-[2-methylprop-1-en-1-yl]-4-methyltetrahydropyran isomers, of the formulae Z-I and E-I ##STR1## containing not less than 85% of Z-I and not more than 15% of E-I, is prepared by a process wherein 2-[2-methylprop-1-en-1-yl]-4-methylenetetrahydropyran of the formula II ##STR2## is hydrogenated over a platinum dioxide or platinum/charcoal catalyst in the presence of a strongly acidic cation exchanger. The product is a useful fragrance material which also occurs naturally and is known as rose oxide.

Preparation of rose oxide predominantly containing the Z isomer

New 1-acyl- and 1-hydroxymethyl-cyclododecanes and -cyclododecenes. The new 1-acyl-cyclododecenes and -cyclododecanes are obtained by a Rupe or Meyer-Schuster rearrangement, with or without subsequent hydrogenation in the presence of Ni, Pd and Pt catalysts. The 1-acyl-cyclododecenes and -cyclododecanes are valuable scents of the basic type of the sought-after macrocyclic musk scents. Furthermore, they are used for the manufacture of numerous other new 1-substituted or 1-and 2-substituted cyclododecenes and cyclododecanes having good scent characteristics.

Musk-like scents and their manufacture

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.

Preparation of bicyclic enol-ethers, and novel ethers of

New macrocyclic ketolactones, especially 15-methyl-15-ethyl- and 15,15-dimethyl-12-oxo-15-hydroxytetradecanecarboxylic acid lactone. The new ketolactones have an intense and delicate woody musky odor and may be employed as scents and fixatives.

Ketolactones

2,6,10-Trimethyl-dodecan-1-al and its 4,8-diene and processes for their manufacture. The new compounds are manufactured by vinylation or ethynylation and subsequent partial hydrogenation of 2-methyl-butan-1-al, reaction of the resulting 4-methyl-hex-1-en-3-ol with a propenyl ether in the presence of an acid catalyst at elevated temperatures, or reaction of the resulting 4-methyl-hex-1-en-3-ol with an .alpha.-formyl-propionic acid ester at elevated temperatures, subsequent vinylation of ethynylation and partial hydrogenation of the resulting 2,6-dimethyl-oct-4-en-1-al, renewed reaction with a propenyl ether or an .alpha.-formyl-propionic acid ester and -- if desired -- catalytic hydrogenation of the resulting 2,6,10-trimethyl-dodeca-4,8-dien-1-al. The organoleptic properties of the new compounds greatly resemble those of the natural scents and aromas of oranges, namely .alpha.- and .beta.-sinensal. They have the advantage over the sinensals of being more stable to acid and alkali, and are therefore particularly suitable for flavoring, eg., carbonated beverages, or for perfuming alkaline products. In addition they are industrially substantially simpler to produce than are the sinensals.

Growing community of inventors

Neuhofen, Germany

Werner Hoffman