For the glycerol-monoiodohydrins of m.p. 48-49' and 53.5-54.5" new methods of preparation are described, The last-mentioned compound has thus become reasonably accessible for the first time. The statemen,ts in the literature as to the constitution of the first-mentioned compound are discussed. Unambiguous evidence for the constitution of the two compounds is furnished: the compound of m.p. 4 8 -4 9 " is the a-isomer, that of m.p.
53.5-54.5'the !-isomer.A glycerol-monoiodohydrin of m.p. 48-49' was first prepared by Liiders 1 ) by heating glycerol-monochlorohydrin with suitable inorganic iodides, and was brought out under the name of "Alival". The starting material was, without any argumentation, stated to be the sc-chlorohydrin: hence the iodine compound thus obtained was from the very first considered to be glycerol-a-monoiodohydrin. What was evidently the same compound was obtained by Fischer and Pfahler z) upon heating the acetone compound of glycerol-monochlorohydrin, the latter prepared by hydrolysis of epichlorohydrin with water, with sodium iodide in alcoholic solution to 1W0: the alcohol or the sodium iodide must have contained water. Further the compound was obtained by Glattfeld and Klaass), who heated crude glycerola-monochlorohydrin, containing some &isomer, with sodium iodide in acetone solution to 100' (?).These methods of preparation are not very satisfactory. W e have now found that the compound in question can be obtained readily and in a good yield by the action of a concentrated hydroiodic acid solution
Diacylglycerol-a-iodohydrins react smoothly with silver dibenzyl phosphate in the presence of benzene, with the formation of diacylglycerol-*-phosphoric acid dibenzyl esters. Upon hydrogenolysis in alcoholic suspension or solution in the presence of a palladium/active carbon catalyst the latter substances yield the corresponding diacylglycerol-a-phosphoric acids and toluene.
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