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Prins reaction in the synthesis of lignin model compounds. I. Synthesis of guaiacylglycerol and veratrylglycerol

R. Brežný and J. Alföldi

Institute of Chemistry, Slovak Academy of Sciences, 809 33 Bratislava


Abstract:  A simple new route leading to eryř/?ro,r/ireo-l-(3,4-dimethoxyphenyl) and -(4-hydroxy-3-methoxyphenyl) glycerol is described. The starting ß-bromostyrenes were converted to the corresponding 1,3-dioxans by means of a newly modified Prins reaction. Opening of the dioxan ring by acetolysis followed by the exchange of bromine atoms for acetoxy groups, and final deacetylation gave the title substances. The stereochemical course of the Prins reaction is discussed on the basis of p.m.r. data. Mass spectral characteristics and p.m.r. data for the synthetic intermediates are also given.

Full paper in Portable Document Format: 325a684.pdf


Chemical Papers 32 (5) 684–690 (1978)

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