ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
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)