Patent GB-875761-A (GB)
Title: Polyene alcohols and acyl derivatives of same and a process for the manufacture thereof
Inventor: ISLER OTTO
IPC: A23L1/275
Filed: 1958-08-28
Abstract: The invention comprises alcohols of the general formula: <FORM:0875761/IV (b)/1> wherein a represents 0 or an integer from 1 to 3 and b represents 0 or the integer 1 and esters thereof with alkanoic acids; alcohols of the general formula:  <FORM:0875761/IV (b)/2> wherein d is 0 or the integer 1 or 2 and e is 0 or the integer 1, the total of d and e not being more than 2 and acyl derivatives of the general formula:  <FORM:0875761/IV (b)/3> wherein a denotes 0 or an integer from 1 to 3 b denotes 0 or the integer 1 and "acyl" denotes an alkanoyl radical and a process for the manufacture of polyene alcohols and acyl derivatives thereof which comprises reducing an aldehyde of the general formula <FORM:0875761/IV (b)/4> wherein the broken line denotes an optional bond, a denotes 0 or an integer of from 1 to 3 and b denotes 0 or the integer 1, by treatment with an alkali-metal hydride and, if desired, treating the resulting alcohol with an acylating agent derived from an alkanoic acid.  The reduction may be carried out with lithium aluminium hydride or sodium boron hydride or potassium boron hydride.  The hydride is preferably employed in a solvent e.g. lithium aluminium hydride in ether or tetrahydrofuran or the sodium or potassium hydrides in an aqueous alcohol or in dioxane may be used.  At the conclusion of the reaction the excess hydride may be destroyed by the addition of water and ethyl acetate or ether.  Acylating agents mentioned include anhydrides or halides of organic acids, especially anhydrides or chlorides of alkanoic acids such as acetic, propionic, butyric or palmitic acid, in the presence of an organic base, such as pyridine, quinoline, dimethyl aniline or methylamine.  The preparation is described in examples of an alcohol of the invention having a C23 side chain with an acetylenic and ethylenic linkages and other alcohols having C21, C23, C26, C28 and C31 side chains with ethylenic linkages and the corresponding acetates.  Aldehydes for use as starting materials may be prepared by processes set forth in Specifications 836,961, 845,819, 850,501 and 866,692.  2 - Methyl-3-isopropoxy-propen-(2)-al-(1) is obtained by condensing ethyl orthoformate with ethyl propenyl ether in the presence of boron trifluoride etherate to form 1,1,3,3-tetraethoxy-2-methyl-propane, hydrolysing the latter and etherifying the free methyl malonic dialdehyde formed by Azeotropic distillation with benzene and isopropanol in the presence of p-toluene-sulphonic acidALSO:Poultry feeding stuffs comprise as an additive for colouring egg yolk, or pigmentation of the shanks beak, skin, fat and flesh of the fowl, a polyene alcohol or acyl derivative thereof obtained by reducing an aldehyde of the general formula <FORM:0875761/I/1> wherein the broken line denotes an optional bond, a denotes 0, 1, 2 or 3 and b denotes 0 or 1, by treatment with an alkali metal hydride, and optionally treating the resulting alcohol with an acylating agent derived from an alkanoic acid (see Group IV(b)).ALSO:Foodstuffs comprise as a colouring matter a polzene alcohol or acyl derivative thereof obtained by reducing an aldehyde of the general formula <FORM:0875761/VI/1> wherein the broken line denotes an optional bond, a denotes 0, 1, 2 or 3 and b denotes 0 or 1, by treatment with an alkali metal hydride and optionally treating the resulting alcohol with an acylating agent derived from an alkanoic acid (see Group IV (b)).