85774-50-1Relevant articles and documents
The chlorination of dihydroconiferyl alcohol
McKague, A. Bruce,Rettig, Steven J.,Trotter, James,Douglas, George R.,Nestmann, Earle R.
, p. 545 - 549 (2007/10/02)
Aqueous chlorination of dihydroconiferyl alcohol, a phenol present in pulping liquors, gave a mixture of three products.The two major products, which formed an inseparable mixture, yielded the crystalline epoxides 1 and 8 when reacted with diazomethane.The epoxide 1 had previously been obtained by reacting one of the components isolated from mutagenic fractions of chlorination-stage effluent from a bleached kraft pulp mill with diazomethane.The result indicate dihydroconiferyl alcohol retained with pulp is chlorinated in the bleach plant to give a mixture of the spirocyclohexenediones 5 and 6.Crystals of 8 are orthorombic, a=24.3048(15), b=12.5403(9), c=7.8653(6) Angstroem, Z=8, space group Pbca.The structure was solved by direct methods and was refined by full-matrix least-squares procedures to R=0.029 and Rw=0.035 for 1308 reflections with I>=3?(I).The structure analysis shows that 8 has the same relative stereochemistry as that reported earlier for 1, but exists as a different conformer in the solid state.