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A convenient synthesis of CIS/trans‐3‐chloroacrylic acid‐UL‐ 14 C
Author(s) -
Roth G. A.,
McKendry L. H.
Publication year - 1988
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.2580250914
Subject(s) - chemistry , methylene , allylic rearrangement , alcohol , aqueous solution , carboxylic acid , chloride , alcohol oxidation , allylic alcohol , organic chemistry , oxide , catalysis
A convenient method for oxidation of allylic alcohols to the corresponding carboxylic acids is described. A two phase (methylene chloride/aqueous) silver oxide oxidation circumvents isolation of the intermediate aldehydes, thus making the procedure well suited to microscale carbon‐14 synthesis. Although we required a mixture of cis/trans‐3‐chloro‐acrylic acid‐UL‐ 14 C and thus began the preparation with cis/trans‐3‐chloroallyl alcohol‐UL‐ 14 C, the reaction sequence can be carried out starting with either isomer to provide the isomerically pure carboxylic acids.