Synthesis of 14C-coniferyl alcohol (4-hydroxy-3-methoxycinnamyl alcohol)

Abstract

SUMMARYConiferyl alcohol-6-14C o r -y-14~ (Iva o r IVb) was prepared by t h e reduction of methyl 4-acetylferulate-6-14C o r y -W (

Studies on the nature and identity of bound chloroaniline residues in plants

“…Incorporation of Chloroaniline Compounds into Synthetic Lignin: A Model System. Coniferyl alcohol (4-hydroxy-3-methoxycinnamyl alcohol) was prepared from 4-hydroxy-3-methoxycinnamic acid (ferulic acid) as described by Baiba and Still (1978) and polymerized with or without [uC]chloroaniline compounds. Three 2-L reservoirs (A, B, and C) were used to feed a proportioning pump.…”

“…In order to pinpoint the carbon atom in the side chain that was binding with the aniline nitrogen, we undertook specific 14C labeling of each carbon in the chain. [/3-14C]-and [>-14C]coniferyl alcohols were prepared (Baiba and Still, 1978) and copolymerized with nonradioactive 3-chloroaniline. The copolymer was analyzed by Py-GC.…”

Syntheses of (1,2-13C), (1-13C) and (3-13C) Coniferyl Alcohol

“…As previously mentioned, only one route leading to the synthesis of (l-13 C) coniferyl alcohol 2e has been published (Balba and Still 1978). However, since the yield reported was so low («1%), no-one has repeated the work to date.…”

“…To date, only one synthesis of (1-14 C) coniferyl alcohol 2a has been reported (Balba and Still 1978). This was achieved, in somewhat desperate means, by condensation of (1-14 C) acetic anhydride with 4acetylvanillin (Perkin reaction) to give methyl 4acetyl (1-14 C) ferulate in about 1% radiochemical Authors to whom correspondence should be addressed.…”