Basf Aktiengesellschaft

Werner Hoffmann

Manfred Baumann

Karl Von Fraunberg

Klaus Schoettle

Lothar Janitschke

Walter Himmele

Joachim Paust

Frank Thoemel

Eduard Kaemmer

Hardo Siegel

Walter Gramlich

Dieter Degner

Lothar Gliniorz

Peter Dobler

Phillip A Rossy

Leopold Hupfer

Ludwig Schuster

Werner Aquila

Sigberg Pfohl

Norbert Mueller

Helmut Lewin

Hubert Sauter

Rolf Hartmuth Fischer

Norbert Goetz

Rainer Becker

Wolfgang Rohr

Johann Jung

Hansgeorg Ernst

Manfred Stroezel

Wolfgang Krause

Hans-Juergen Raubenheimer

Klaus Boehlke

Juergen Varwig

Hartwig Fuchs

Heinz-Guenter Oeser

Juergen Paetsch

Bernd Meissner

Karl Hennig

Wolfgang Lengsfeld

Ernst Langguth

Lothar Arnold

Hans-Ulrich Scholz

Karlheinz Messmer

Hans-Juergen Scheiper

Klaas Jansen

Jens-Uwe Bliesener

Gerhard Kleinpeter

Guenter Hoerdt

A process for the preparation of a 5-vinylpyrrolidone of the formula ##STR1## wherein each of R.sup.1 and R.sup.2 is hydrogen or alkyl and R.sup.3 is preferably hydrogen but may further represent alkyl, cycloalkyl, aryl, alkylaryl, arylalkyl or a 5- to 6-membered aromatic or non-aromatic heterocyclic group containing 1 to 3 nitrogen atoms and/or an oxygen or sulfur atom, the process being carried out in two steps, first to react a 3-formylpropionic acid ester of the formula ##STR2## where each of R.sup.1 and R.sup.2 is hydrogen or C.sub.1 -C.sub.8 -alkyl, and R.sup.4 is hydrogen, alkyl, cycloalkyl, aryl, alkylaryl or arylalkyl, with a vinylymagnesium halide of the formula

Preparation of 5-vinylpyrrolidones

A process for preparing canthaxanthin (Ia) and astaxanthin (Ib) of the formula I ##STR1## where R is H (a) or OH (b), comprises reacting a tertiary alcohol of the formula II ##STR2##

Preparation of canthaxanthin and astaxanthin

The preparation of 3-alkoxycarbonyl propenals and 3-dialkoxymethyl propenals of the general formulae Ia and Ib respectively: ##STR1## (R.sup.1 =C.sub.1 -C.sub.3 -alkyl group; R.sup.2 and R.sup.3 =hydrogen, methyl, or ethyl; and R.sup.4 and R.sup.5 =C.sub.1 -C.sub.4 -alkyl groups, which may be joined to form a 5-membered or 6-membered ring), is effected by reacting a corresponding alcohol of the general formula IIa or IIb ##STR2## with oxygen or an oxygen-containing gas in the gas phase in the presence of a metal from Group IB of the Periodic Table or a compound of one such metal acting as catalyst. The target products serve as intermediates for the synthesis of carotenoids.

Preparation of 3-alkoxycarbonyl propenals and 3-dialkoxymethyl propenals

Diethers of m- or p-hydroxyphenol, as well as the monoethers, are prepared by reacting m- or p-tert.-butoxyphenol of the formula II ##STR1## with a halogen compound in the presence of a hydroxide, carbonate and/or bicarbonate of an alkali metal or alkaline earth metal and an organic solvent which is inert under the reaction conditions, at from 20.degree. C. to 150.degree. C., and, if desired, reacting the resulting diether with a dilute aqueous inorganic acid at from 30.degree. to 100.degree. C. to give the monoether. The end products which can be prepared by the process according to the invention are useful starting materials for the preparation of dyes, drugs and crop protection agents.

Diethers of m- or p-hydroxyphenol

Process for the preparation of the compounds of the formulae Ia and Ib ##STR1## wherein A. 2,4,4-trimethylcyclohex-2-en-1-one oxime of the formula IIb ##STR2## is treated with a strong aqueous acid at from 30.degree. to 80.degree. C., preferably from 40.degree. to 70.degree. C.,

Novel preparation of compounds of the 4-oxodamascone series, and novel

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

2-tert-butyl-4-methylcyclohexanol is used as a scent and as a component of scent compositions. Scent compositions contain 2-tert-butyl-4-methylcyclohexanol (I), which influences their fragrance. It has a very intense earthy woody vetiver-like fragrance and is stable in neutral, acidic and alkaline solutions.

Use of 2-tert-butyl-4-methylcyclohexanol as a scent and as a component

A horizontal solid-bed polymerization reactor which is divided into a plurality of zones, for example a reaction zone, an after-reaction zone, a heating zone and a product discharge zone and possesses inlet and outlet openings for feeding substances into the zones and/or removing substances from the zones, the zones being separated from one another over a part of the reactor cross-section by means of weirs, wherein two drive shafts which are independent of one another and possess mixing elements are introduced into the solid-bed polymerization reactor in the middle.

Apparatus for the solid-bed polymerization of monomers

Novel disubstituted bicyclo[2.2.1]heptanes of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.3 -alkyl, R.sup.2 is C.sub.1 -C.sub.8 -alkyl or-alkenyl, R.sup.3 and R.sup.4 together are .dbd.O, .dbd.CH--CN, .dbd.CH--CO--OCH.sub.3 or .dbd.CH--CO--OC.sub.2 H.sup.5, or R.sup.3 is hydrogen, --CH.sub.3, --CH.dbd.CH.sub.2 or --C.tbd.CH when R.sup.4 is --OH or --O--CO--CH.sub.3, or R.sup.3 is H when R.sup.4 is --CH.sub.2 --CO--OCH.sub.3, --CH.sub.2 --CO--OC.sub.2 H.sub.5 or --CH.sub.2 --C.tbd.N and one or both of the dashed lines may be a further bond, are obtained by subjecting cyclopentadiene to a Diels-Alder reaction with an unsaturated ketone, this reaction being catalyzed by a Lewis acid, and then subjecting the compound of the formula Ia ##STR2## initially formed to a reduction, a Grignard reaction or a reaction with diethylphosphonoacetonitrile or ethyl phosphonoacetate and NaH. They can be used as scents and/or aromas or as intermediates for scents.

Novel 2,3-disubstituted bicyclo(2.2.1)heptanes and heptenes, their

Acetylene compounds of the formula ##STR1## where R.sup.1, R.sup.2 and X have the meanings given in the description, a process for their preparation and their use for regulating plant growth.

Acetylene compounds, their preparation and their use for regulating

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

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

4-Substituted but-3-ene-1-carboxylic acids and their esters R.sup.1 R.sup.2 C.dbd.CH--CH.sub.2 --CO--O--R.sup.3 (I, where R.sup.1 is an organic radical, R.sup.2 is H or R.sup.1, or R.sup.1 and R.sup.2 together form a 5-membered to 20-membered ring, and R.sup.3 is H or lower alkyl) are prepared by carbonylation of R.sup.1 R.sup.2 C(OH)--CH.dbd.CH.sub.2 (II) in the presence of an alcohol R.sup.3' --OH (III, where R.sup.3' is lower alkyl) or, for the preparation of the acids I alone, in the absence of an alcohol III, at from 50.degree. to 150.degree. C. and under from 200 to 700 bar, using a complex of a palladium halide and a tertiary organic phosphine.

Preparation of 4-substituted but-3-ene-1-carboxylic acids and their

Process for the preparation of the compounds of the formulae Ia and Ib ##STR1## wherein A. 2,4,4-trimethylcyclohex-2-en-1-one oxime of the formula IIb ##STR2## is treated with a strong aqueous acid at from 30.degree. to 80.degree. C., preferably 40.degree. to 70.degree. C.,

Preparation of compounds of the 4-oxodamascone series, and novel scents

1-Formyl-2,6,6-trimethyl-cyclohex-1-ene derivatives of the formula I ##STR1## where R is --H or --CH.sub.3 and A is O or NOH are prepared by nitrosylating the corresponding 1-formyl-2,6,6-trimethyl-cyclohex-1-ene or -cyclohex-2-ene and, where appropriate, hydrolyzing the resulting oxime (where A is NOH) to the corresponding ketone (where A is O). The compounds I, except where R is H and A is O, are novel.

1-Formyl-tri- and tetramethyl-cyclohex-1-en-3-one oximes

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Neuhofen, Germany

Werner Hoffmann