Abstract
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.
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6 articles.
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