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Home Molecular Biology Process-for-preparing-substituted-cyclic-acetals-of-oxyacetaldehydes-and-said-cyclic-acetals

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 Process for preparing substituted cyclic acetals of oxyacetaldehydes and said cyclic acetals

Details
Inventors: Sprecker, Mark A.; Kryschuk, John J.; Hall, John B.;
Assignee: International Flavors & Fragrances Inc. (New York, NY)
Primary Examiner: Love; Ethel G.
Assistant Examiner:
Attorney, Agent or Firm: Liberman; Arthur L.

A process is described for the preparation of substituted oxyacetaldehydes and cyclic acetals thereof according to the reaction sequence: ##STR1## wherein R.sub.1 and R.sub.2, taken together form a lower alkylene group; wherein R.sub.3 is alkyl, alkenyl or alkadienyl and X is halogen selected from the group consisting of chlorine and bromine, the reaction (i) being carried out (1) using a "phase transfer agent" and (2) in a two phase system.

DETAILED DESCRIPTION What is claimed is: 1.
A process for preparing citronellyl oxyacetaldehyde alkylene acetal according to the reaction: ##STR25## comprising the steps of (a) intimately admixing citronellol with chloroacetaldehyde alkylene acetal in the presence of a base which is sodium hydroxide and a phase transfer agent which is tricapryl methyl ammonium chloride; the reaction temperature being in the range of from 120.
degree.
C.
up to about 200.
degree.
C.
; the mole ratio of citronellol to chloroacetaldehyde alkylene acetal being from 0.
5:1 up to 2:1, the mole ratio of citronellol to base being between 1:1 and 1:2; the concentration of tricapryl methyl ammonium chloride phase transfer agent in the reaction mass based on amount of chloroacetaldehyde alkylene acetal being in the range of from 0.
5 grams of tricapryl methyl ammonium chloride per mole of chloroacetaldehyde alkylene acetal up to 25 grams of tricapryl methyl ammonium chloride per mole of chloroacetaldehyde alkylene acetal; the reaction being carried out in the absence of solvent or in the presence of a solvent selected from the group consisting of xylene and decalin; and (b) fractionally distilling the resulting product hereby citronellyl oxyacetaldehyde alkylene acetal is recovered from the distillate; wherein ##STR26## is the citronellyl moiety; wherein R.
sub.
1 and R.
sub.
2 taken together form an alkylene moiety having from 2 up to 4 carbon atoms and wherein X is chloro.
2.
A process for preparing a mixture of geranyl oxyacetaldehyde and neryl oxyacetaldehyde according to the reaction sequence: ##STR27## comprising the steps of (a) intimately admixing a mixture of geraniol and nerol with chloroacetaldehyde alkylene acetal in the presence of a base which is sodium hydroxide and a phase transfer agent which is tricapryl methyl ammonium chloride; the reaction temperature being in the range of from 120.
degree.
C.
up to about 200.
degree.
C.
; the mole ratio of mixture of geraniol and nerol to chloroacetaldehyde alkylene acetal being from 0



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