Preparation of alkenols
AssigneeBASF SE
InventorsUlrich Klein, Ernst Buschmann, Christiane Mackenroth
Life of this patent
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Abstract
A process for preparing alkenols of the formula I R.sup.1 --CH.dbd.CH(CH.sub.2).sub.n OH I where R.sup.1 is hydrogen or a hydrocarbon radical, and n is an integer from 3 to 15, a) by reacting a phosphonium salt of the formula IIa R.sup.1 --CH.sub.2 --P.sup.+ (C.sub.6 H.sub.5).sub.3 X.sup.-IIa where X is chlorine, bromine or iodine, with an aldehyde of the formula IIIa or its hemiacetal of the formula IIIb ##STR1## or b) by reacting a phosphonium salt of the formula IIb (C.sub.6 H.sub.5).sub.3 P.sup.+ (CH.sub.2).sub.n+1 OH X.sup.-IIb with a aldehyde of the formula IV R.sup.1 CHO IV in a solvent in the presence of a base, wherein the base is the alkali metal salt of an alcohol and the solvent is an alcohol.
Claims9
A process for preparing alkenols of the formula I
- R.sup.1 --CH.dbd.CH(CH.sub.2).sub.n OH I
- where R.sup.1 is hydrogen or an alkyl of 1-20 carbons or a cycloalkyl of 3-17 carbons, and n is an integer from 3 to 15,
- a) by reacting a phosphonium salt of the formula IIa
- R.sup.1 --CH.sub.2 --P.sup.+ (C.sub.6 H.sub.5).sub.3 X.sup.-IIa
- where X is chlorine, bromine or iodine, with an aldehyde of the formula IIIa or its hemiacetal of the formula IIIb ##STR9## or b) by reacting a phosphonium salt of the formula IIb
- (C.sub.6 H.sub.5).sub.3 P.sup.+ (CH.sub.2).sub.n+1 OH X.sup.-IIb
- with an aldehyde of the formula IV
- R.sup.1 CHO IV
- in a solvent in the presence of a base, wherein the base is the alkali metal salt of an alcohol and the solvent is an alcohol.
A process for preparing 5-decen-1-ol by reacting n-pentanol with a hydrohalic acid to give the corresponding pentyl halide, subsequently reacting the pentyl halide with triphenylphosphine to give the corresponding pentyltriphenylphosphonium salt and condensing the phosphonium salt with 5-hydroxypentanal or 2-hydroxytetrahydropyran in the presence of a base, wherein this sequence of reactions is carried out without isolating the intermediates in n-pentanol as solvent.
A process for preparing 4-tridecen-1-ol by reacting n-nonanol with a hydrohalic acid to give the corresponding nonyl halide, subsequently reacting the nonyl halide with triphenylphosphine to give the corresponding nonyltriphenylphosphonium salt and condensing the phosphonium salt with 4-hydroxybutanal or 2-hydroxytetrahydrofuran in the presence of a base, wherein this sequence of reactions is carried out without isolating the intermediates in n-nonanol as solvent.
A process for preparing 8-dodecen-1-ol by reacting 8-bromooctan-1-ol with triphenylphosphine and subsequently condensing the phosphonium salt which is formed with butyraldehyde in the presence of a base, wherein this sequence of reactions is carried out without isolating the intermediates in an alcohol as solvent.
A process for preparing 9-dodecen-1-ol by reacting 9-bromononan-1-ol with triphenylphosphine and subsequently condensing the phosphonium salt which is formed with propionaldehyde in the presence of a base, wherein this sequence of reactions is carried out without isolating the intermediates in an alcohol as solvent.
A process for preparing alkenols of the formula I
- R.sup.1 --CH.dbd.CH(CH.sub.2).sub.n OH I
- where R.sup.1 is hydrogen or an alkyl of 1-20 carbons or a cycloalkyl of 3-17 carbons, and n is an integer from 3 to 15, by reacting a phosphonium salt of the formula IIA
- R.sup.1 --CH.sub.2 --P.sup.+ (C.sub.6 H.sub.5).sub.3 X.sup.-IIa
- where X is chlorine, bromine or iodine, with an aldehyde of the formula IIIA or its hemiacetal of the formula IIIB ##STR10## in a solvent in the presence of a base, wherein the base is the alkali metal salt of an alcohol and the solvent is an alcohol.
A process for preparing alkenols of the formula I
- R.sup.1 --CH.dbd.CH(CH.sub.2).sub.n OH I
- where R.sup.1 is hydrogen or an alkyl of 1-20 carbons or a cycloalkyl of 3-17 carbons, and n is an integer from 3 to 15, by reacting a phosphonium salt of the formula IIb
- (C.sub.6 H.sub.5).sub.3 P.sup.+ (CH.sub.2).sub.n+1 OH X.sup.-IIb
- with an aldehyde of the formula IV
- R.sup.1 CHO IV
- in a solvent in the presence of a base, wherein the base, wherein the base is the alkali metal salt of an alcohol and the solvent is an alcohol.
Dependencies are inferred from the claim text.