Process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals
AssigneeBASF SE
InventorsHansgeorg Ernst, Klaus Henrich
Life of this patent
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Abstract
The invention relates to a process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I which comprises a) condensing an ester phosphonium salt of the general formula II or an ester phosphonate of the general formula III with an aldehyde of the formula IV in a Wittig or Wittig-Horner reaction to give an acetal ester of the general formula V b) reducing the ester of the formula V to give an acetal alcohol of the general formula VI and c) oxidizing the alcohol to 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I, where the substituents have the meaning defined in the description.
Claims10
A process for preparing 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I,
- in which the substituents R1 and R2 may, independently of one another, be C1-C8-alkyl or, together with the oxygen atoms and the carbon atoms to which they are bonded, form a 1,3-dioxolane or 1,3-dioxane ring of the following structures
- in which R3 and R4, and R5 may each, independently of one another, be hydrogen or C1-C4-alkyl,
- which comprises
- a) condensing an ester phosphonium salt of the general formula II or an ester phosphonate of the general formula III,
- in which the substituents have, independently of one another, the following meaning:
- R6 C1-C8-alkyl;
- R7 aryl;
- X− an anion equivalent of an inorganic or organic acid;
- R8 and R9
- C1-C8-alkyl;
- with an aldehyde of the formula IV
- in a Wittig or Wittig-Horner reaction to give an acetal ester of the general formula V,
- in which the substituents R1, R2 and R6 in the compounds IV and V have the abovementioned meaning,
- b) reducing the ester of the formula V to an acetal alcohol of the general formula VI,
- and
- c) oxidizing the alcohol to 2,7-dimethyl-2,4,6-octatrienal monoacetals of the general formula I.
An acetal ester of the formula Va
- in which the substituents have, independently of one another, the following meaning
- R6 C1-C8-alkyl;
- R1 and R2
- together with the oxygen atoms and the carbon atoms to which they are bonded a 1,3-dioxolane or 1,3-dioxane ring of the following structures,
- in which R3 and R4, and R5 may each, independently of one another, be hydrogen or C1-C4-alkyl.
An acetal alcohol of the formula VI
- in which the substituents have, independently of one another, the following meaning:
- R1 and R2
- C1-C8-alkyl or together with the oxygen atoms and the carbon atoms to which they are bonded a 1,3-dioxolane or 1,3-dioxane ring of the following structures,
- in which R3 and R4, and R5 may each, independently of one another, be hydrogen or C1-C4-alkyl.
Dependencies are inferred from the claim text.