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A novel synthesis of isoeugenol, [ring‐(U)‐ 14 C]
Author(s) -
Immoos John E.
Publication year - 2015
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3329
Subject(s) - chemistry , isoeugenol , ring (chemistry) , phenols , carboxylate , ether , dimethylformamide , alkyl , medicinal chemistry , williamson ether synthesis , organic chemistry , stereochemistry , eugenol , solvent
A novel method for the preparation of isoeugenol, [ring‐(U)‐ 14 C] is presented. Phenols and phenyl esters substituted in the para position with 1‐hydroxyethyl or 1‐hydroxypropyl acetate esters when treated with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene in dimethylformamide (DMF) eliminate the alkyl carboxylate function to give the unsaturated compound. The reaction fails with unsubstituted or ether substituted phenyl 1‐hydroxyacetate esters.