Synthesis and properties of some O-(2,2-dialkoxyethyl)glycolaldehydes

✍ Scribed by F.J.Lopez Aparicio; F.Zorrilla Benitez; F.Santoyo Gonzalez

• Publisher: Elsevier Science
• Year: 1983
• Tongue: English
• Weight: 441 KB
• Volume: 114
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(83)88196-8

✦ Synopsis

The reaction of bromoacetaldehyde dialkyl acetals and the monosodium salt of glycerol gave mixtures of the 0-( 2,3-dihydroxypropyl)glycolaldehyde dialkyl acetals (la-e) and O-( I ,3-dihydroxy-2-propyl)g~ycolaldehyde dialkyl acetals (Za-c). The components were identified, after acetylation, by comparison (t.l.c., Lr., and 'Ii-n.m.r. data) with the authentic compounds described below. When the mixtures of diols were oxidised with aqueous periodate, the corresponding O-(2,2_dialkoxyethyl)-gIycolaldehydes (3-a-c) were obtained in good yietd by distillations and acetylation of the residue then gave the corresponding O-( 1,3-diacetoxy-&propyl)glycolaldehyde dialkyl acetal. The aldehydes 3a,b were also prepared from 2,3~~-isopropylideneglycerol by application, in sequence, of O-alkyiation with bromoacetaldehyde diethyl acetal, reaction with ~thanethiol in hydrochloric acid to give ~-(2,3-dihydroxypropyl)glycolaldehyde diethyl dithioacetal (4), acetylation, treatment with the corresponding alcohol in the presence of HgCl, and HgO, transesterification (MeONa-MeOH), and periodate oxidation.