DE876241C - Process for the production of fragrances from terpene phenols - Google Patents

Description

Process for the production of fragrances from terpene phenols Like in patent 86o 946, whose claim reads: Process for the production of fragrances from terpene phenols, characterized in that terpene phenols are reduced catalytically and optionally the terpene cyclohexanols obtained to give the corresponding ketones oxidized, is described, the hydrogenation products of terpene phenols are valuable Odoriferous substances.

As has now been further found, such are also hydrogenated terpene phenols or the corresponding ketones can be used for the same purpose in which the Oxy group of the cyclohexane residue is etherified, as well as those in which beside an alkoxy group still has a second free or etherified oxy group. In particular, the condensation of guaiacol and guathol and subsequent Compounds obtained by hydrogenation, namely i-oxy-2-methOxy-4-camphylcyclohexane and i-oxy-2-ethoxy-4-camphylcyclohexane as extremely valuable, despite the has a strong smelling high boiling point and is largely similar to the natural sandalwood oil Products proven. So are the ketones obtainable from these alcohols valuable products, the smell of which is more towards the vetiver.

Example iooo parts of i-oxy-2-methoxy-4-camphylbenzene with a boiling point of .e = 205 to 2i5 ° (obtainable by condensation of guaiacol with camphene using boron fluoride) are mixed with 3o parts of a highly active nickel catalyst at q0 at and 18o to 2oo ° treated with hydrogen for several hours. 87o parts of z-oxy-2-methoxy-q.-camphylcyclohexane with a boiling point of 7-8 = igo to 1g5 ° are obtained as a colorless, viscous liquid with an excellent smell of sandalwood oil.

300 parts are stirred with 600 parts of glacial acetic acid and 150 parts of water and in one to one and a half hours I20 parts of sodium dichromate, in 36o parts of 500% sulfuric acid dissolved, added at: 20 to 25 ° and stirred for a further hour, this gives after dilution with water, separation of the oil and fractional distillation in Vacuum 225 parts of that at i7ö to i75 ° below q. i-Oxo-2-methoxy-q.-camphylcyclohexane boiling up to 5 mm pressure with a pleasant smell of sandalwood oil, tending towards vetiver.

In the same way, by condensation of camphene with Guäthol the i-oxy-2-ethoxy-4.-camphylbenzene with b.p. "= 215 to 225 °. By hydrogenation the i-oxy-2-ethoxy-4-camphylcyclohexane is obtained therefrom with a boiling point of 4_5 = 2io to 2i5 ° with a fine, strong smell of sandalwood oil. This can be converted into the corresponding ketone convict. Furthermore, similar, albeit somewhat weaker-smelling compounds can be found obtained if the camphene with resorcinol monomethyl ether, hydroquinone monomethyl ether, Anisole and veratrole condensed and the condensation product hydrogenated and optionally oxidized to the ketone.

Instead of camphene, terpenes such as pinene and dipentene, kcrrrren for use. It can also be used instead of the terpenes alcohols such. B. Borneol or isoborneol, with heating in the form of active earth for condensation be used with the raced phenolic ethers.

Claims (1)

PATENT CLAIM: Process for the production of fragrances from terpene phenols according to patent 86o 946, characterized in that such terpene-plicnols are catalytically reduced and, if necessary, then oxidized to the corresponding ketones, whose hydroxyl group is etherified and which also have a further free or may also contain etherified hydroxyl groups.