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Juergen Frank

Franz Merger

Rolf Hartmuth Fischer

Joachim Paust

Thomas Kuekenhoehner

Eckhard Hickmann

Udo Rheude

Hans-Juergen Weyer

Bernhard Schulz

Eberhard Ammermann

Gisela Lorenz

Karl-Otto Westphalen

Bruno Wuerzer

Karl Eicken

Joachim Rheinheimer

Jochem Henkelmann

Norbert Meyer

Wolfgang Hoelderich

Thomas Zierke

Hans Theobald

Toni Dockner

Hardo Siegel

Uwe Vagt

Michael Roeper

Manfred Sauerwald

Hans Horler

Thomas Ruehl

Uwe Vagi

2-Methyl-1,4-butanediol and 3-methyltetrahydrofuran are prepared by reacting a compound of the general formula I or II ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or C.sub.1 -C.sub.8 -alkyl and the formyl group of II may also be present as acetal with a C.sub.1 -C.sub.8 -alkanol, is reacted with hydrogen in the presence of copper or of a metal of groups 7 to 10 of the Periodical Table of elements or of a compound of these metals.

Preparation of 2-methyl-1,4-butanediol and 3-methyltetrahydrofuran

A process of preparing symmetric C.sub.40 -carotenoids by reacting a C.sub.15 -triphenylphosphonium salt of the formula ##STR1## and a 2,5-bis(1,1-dialkoxy-2-propyl)-2,5-dihydrofuran to form a reaction product containing a diacetyl and a triphenylphosphonium salt, adding a strong base to the reaction product to convert the triphenylphosphonium salt to a carbenium ion, hydrolyzing the diacetyl to a dialdehyde, subjecting the dialdehyde and the carbenium ion to a Wittig reaction to prepare a Wittig reaction product, and converting the Wittig reaction product to the C.sub.40 -carotenoid by acid treatment.

2,5-bis(1,1-dialkoxy-2-propyl)-2,5-dihydrofurans, the preparation

2,5-bis(1,1-dialkoxy-2-propyl)-2,5-dihydrofurans of the formula I ##STR1## where R.sup.1 and R.sup.2 can be identical or different and can be alkyl of 1 to 4 carbons, the preparation thereof by reaction of 2,5-dialkoxy-2,5-dihydrofurans of the formula II ##STR2## In the presence of protic acids or Lewis acids with an alkyl propenyl ether of the formula III ##STR3## and the use thereof for preparing 2,7-dimethyl-2,4,6-octatrienedial and symmetric C.sub.40 -carotenoids such as .beta.-carotene, canthaxanthin and astaxanthin, are described.

A 3-substituted 2-hydroxy-3-formylpropionic ester of the formula I ##STR1## where R.sup.1 is lower alkyl, and R.sup.2 is straight-chain or branched alkyl of 1 to 10 carbon atoms, is obtained by adding an alkanal of the fomrula II ##STR2## and an alkyl glyoxylate of the formula III ##STR3## simultaneously to a catalyst system composed of a salt or a mixture of a secondary amine and a carboxylic acid in such a way that the temperature does not exceed 90.degree. C., preferably 80.degree. C., or else adding one of the reactants of the formula II or III to a mixture of the catalyst system described above and the other reactant in such a way that the temperature does not exceed 90.degree. C. The 2-hydroxy-3-formylpropionic eater of the formula I can be converted by treatment with dehydrating agents, especially acetic anhydride, into good yields of the corresponding 3-substituted 3-formylacrylic ester.

3-substituted 2-hydroxy-3-formylpropionic esters, the preparation

A 3-substituted 2-hydroxy3-formylpropionic ester of the formula I ##STR1## where R.sup.1 is lower alkyl, and R.sup.2 is straight-chain or branched alkyl of 1 to 10 carbon atoms, is obtained by adding an alkanal of the formula II ##STR2## and an alkyl glyoxylate of the formula III ##STR3## simultaneously to a catalyst system composed of a salt or a mixture of a secondary amine and a carboxylic acid in such a way that the temperature does not exceed 90.degree. C., preferably 80.degree. C., or else adding one of the reactants of the formula II or III to a mixture of the catalyst system described above and the other reactant in such a way that the temperature does not exceed 90.degree. C. The 2-hydroxy-3-formylpropionic ester of the formula I can be converted by treatment with dehydrating agents, especially acetic anhydride, into good yields of the corresponding 3-substituted 3-formylacrylic ester.

A process for the preparation of 4-acetals of butene-1,4-dial of the formula ##STR1## where R is an alkyl, alkenyl, cycloalkyl or aralkyl radical of 1 to 12 carbon atoms which may contain alkoxy groups, or the two radicals R together form an alkylene or alkenylene radical of 2 to 10 carbon atoms which may contain alkoxy groups, and R.sup.1 is an alkyl, alkenyl or alkynyl radical of 1 to 12 carbon atoms which may be substituted by cycloaliphatic, aromatic or heterocyclic radicals or by hydroxyl, ether, thioether, acyl, alkylamino, carboxyl or carbalkoxy groups, or is an unsubstituted or substituted aryl radical or an alkoxy, alkylthio or acyloxy group, wherein a glyoxal monoacetal of the formula ##STR2## is reacted with an aldehyde of the formula

Preparation of 4-acetals of butene-1,4-dial and novel acetals of

5-(1,2,4-Triazol-1-yl-methyl)-isoxazolines I ##STR1## where R.sup.1 and R.sup.2 are each H, alkoxyalkyl, haloalkyl, alkyl, cycloalkylalkyl, phenylalkyl, naphthylalkyl, cycloalkyl, phenyl, naphthyl or hetaryl, where the aryl and hetaryl moieties of the stated substituents may furthermore carry an unsubstituted or halogen-substituted phenyl or phenoxy radical or up to 3 of the following radicals: halogen, CN, NO.sub.2, alkyl, haloalkyl or alkoxy, and the salts and metal complexes of I are suitable as fungicides and for regulating plant growth.

5-(1,2,4-triazol-1-ylmethyl)-isoxazolines

Mixtures which contain 1,4-butanediol and tetrahydrofuran are prepared by heating 4-hydroxybutyraldehyde of the formula ##STR1## at 20.degree.-300.degree. C. in the presence or absence of 1,4-butanediol and subjecting the resulting acetals of the formulae ##STR2## to a catalytic hydrogenation at 50.degree.-300.degree. C. and 1-350 bar.

Preparation of 1,4-butanediol and tetrahydrofuran

Cyclic 6-membered to 8-membered 1,2-vinylenedioxy compounds of the general formula I ##STR1## where A is ##STR2## R.sup.1 to R.sup.7 independently of one another are each hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.16 -alkoxyalkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, C.sub.5 -C.sub.8 -cycloalkyl, aryl, C.sub.7 -C.sub.10 -alkylphenyl, C.sub.7 -C.sub.10 -phenalkyl, C.sub.8 -C.sub.10 -phenalkenyl or a heterocyclic structure, or R.sup.2 and R.sup.3, R.sup.2 and R.sup.4, R.sup.3 and R.sup.4, R.sup.2 and R.sup.6, R.sup.3 and R.sup.6, R.sup.4 and R.sup.5 or R.sup.6 and R.sup.7 together form a cycloaliphatic or heterocyclic ring, and R.sup.1 to R.sup.7 may furthermore carry substituents which are inert under the reaction conditions, and n is 0 or 1, are prepared by a process in which a cyclic 2-oxymethyl-1,3-dioxa compound or one of its derivatives of the general formula II ##STR3## where R.sup.1 to R.sup.7, A and n have the abovementioned meanings, and R.sup.8 is hydrogen or C.sub.1 -C.sub.12 -alkyl, is converted in the presence of an acidic catalyst at from 150.degree. to 450.degree. C. and under from 0.001 to 50 bar, some of the compounds obtained being novel.

Preparation of cyclic 6-membered to 8-membered vinylene-1,2-dioxy

Isoxazolines of the general formula I ##STR1## where the substituents have the following meanings: R.sup.1 is C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.7 -cycloalkyl, substituted or unsubstituted phenyl, or a saturated or unsaturated 5- or 6-membered heterocycle;

Isoxazolines, their preparation and their use

Pentenoic esters are prepared by a process in which 4- and/or 3-formylvaleric esters are heated to 50.degree.-400.degree. C. in the presence of a catalyst which contains one or more elements of subgroup VIII of the Periodic Table.

Preparation of pentenoic esters from formylvaleric esters

2(5H)-furanones I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.7 -C.sub.12 -aralkyl or aryl, are prepared by heating a 3-formylcarboxylate or 3-formylcarboxylic acid II ##STR2## where R.sup.3 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.5 - or C.sub.6 -cycloalkyl, C.sub.7 -C.sub.12 -aralkyl or aryl, to 100.degree.-450.degree. C. in the presence of an acidic catalyst.

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Juergen Frank