
%0 Journal Article
%A Chan, HTJ 
%A Elix, JA 
%T Annelated furans. XII. Fries rearrangement of isocreosol esters
%J Australian Journal of Chemistry
%D 1973/05/01
%V 26
%N 5
%P 1069-1078
%K 
%R https://doi.org/10.1071/CH9731069
%U https://www.publish.csiro.au/paper/CH9731069 
%X The Fries reaction of 2-methoxy-5-methylphenyl butyrate (5) in the presence of titanium tetrachloride gave only the para rearrangement product, 4-hydroxy-5-methoxy-2-methylphenyl propyl ketone (6). Irradiation of the ester (5) gave the ortho rearrangement product, 2- hydroxy-3-methoxy-6-methylphenyl propyl ketone (7), in addition to (6), isocreosol, and 2-hydroxy-4-methylphenyl propyl ketone (8). The photorearrangement of 3-nitropropionate esters of isocreosol and related phenols did not proceed satisfactorily as the 3-nitropropionyl group appeared unstable under these conditions. However, the photo- Fries rearrangement of the corresponding 3-chloropropionate esters proceeded normally with the formation of o- and p-hydroxyphenyl 2- chloroethyl ketones, and in addition the substituted o-hydroxyphenyl vinyl ketones, generated by elimination of hydrogen chloride from the corresponding ortho rearrangement product. 
