Process for the manufacture of a gamma-halotiglic aldehyde

Details Process for the manufacture of a gamma-halotiglic aldehyde Process for the manufacture of a gamma-halotiglic aldehyde

1997-08-01

1998-07-28

Siegel, Alan

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568486, 568488, C07C 4500

Patent

active

057865183

ABSTRACT:
A novel process for the manufacture of a .gamma.-halotiglic aldehyde or bromine, comprises haloalkoxylating a 1-alkoxy-2-methyl-1,3-butadiene signifies C.sub.1-4 -alkyl, using a particular halogenating agent in a C.sub.1-4 -alkanol (R.sup.2 OH) and hydrolyzing the thus-obtained .gamma.-halotiglic aldehyde dialkyl acetal HalH.sub.2 .gamma.-chloro- or .gamma.-bromotiglic aldehyde I. The halogenating agent used in this process is selected from an alkali metal hypochlorite, an alkali metal hypobromite, an alkaline earth metal hypochlorite, an alkaline earth metal hypobromite, tert.butyl hypochlorite, N-bromoacetamide, 1.3-dichloro-5,5-dimethylhydantoin and 1,3-dibromo-5,5-dimethylhydantoin. Further aspects of the present invention are the use of the thus-manufactured .gamma.-halotiglic aldehyde for the production of .gamma.-acetoxy-tiglic aldehyde or of a Wittig aldehyde halide Hal-Ph.sub.3 P.sup.+ CH.sub.2 --CH.dbd.C(CH.sub.3)--CHO as well as a process for the catalytic dealkoxylation of the 1,1,3-trialkoxy-2-methyl-butane CH.sub.3 1-alkoxy-2-methyl-1,3-butadiene II in the gas phase using an aluminium silicate of medium specific surface as the catalyst. The products I, .gamma.-acetoxy-tiglic aldehyde and VII are known, important intermediates for the production of various apocarotenoids and diapocarotenoids as well as of Vitamin A.

REFERENCES:
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