GB738420A - Treatment of alkyl ustilate esters - Google Patents

Abstract

The invention comprises alkyl esters of 15-aldehydopentadecanoate and of 2 - hydroxy-15 - aldehydopentadecanoate, and 2 : 15 - dihydroxypentadecanoic acid, its esters and salts when prepared by the following method; and the method of oxidizing 15 : 16-di-hydroxyhexadecanoic acid esters to convert to an aldehyde by means of a glycol-splitting oxidant, followed by reduction of the product to the 15-hydroxy pentadecanoic esters, or performing the same reactions with 2 : 15 : 16 trihydroxyhexadecanoic acid esters, alone or mixed with the above esters. In examples, methyl 15 : 16 dihydroxyhexadecanoic ester is oxidized with lead tetra-acetate in acetic acid to give methyl 15-aldehydopentadecanoate, which on reduction with Raney nickel gives 15-hydroxypentadecanoic ester from which the acid is obtained by hydrolysis; a crude mixture of the above methyl ester and methyl 2 : 15 : 16-trihydroxy hexadecanoate, known as methyl ustilate mixture, gives by a similar oxidation reduction the two products methyl 2 : 15-dihydroxypentadecanoate (2 - hydroxy - 15 - aldehydo - pentadecanoate being formed intermediately) and 15-hydroxypentadecanoate, the latter of which is hydrolysed to the acid; the 2 : 15 : 16-trihydroxyhexadecanoic methyl ester similarly gives, after reduction, 2 : 15-dihydroxypentadecanoic ester and acid; the ustilic acid methyl ester mixture is also oxidized with Pb3O4 and sodium bismuthate, followed by reduction, to give the same mixture of products as above, and hydrolysis to the acid as above described, if desired. The known 15-hydroxy-compound may be used to produce the synthetic musk, 15-pentadecanolactone.