Titanium Tetrachloride Induced Fries Rearrangement: A New Route to Disubstituted 2'-Hydroxypropiophenones

Article abstract of DOI:10.1055/s-1989-27134

Fries rearrangement of some dialkylphenyl propionates with titanium tetrachloride proves to be a convenient route to hindered dialkyl 2'-hydroxypropiophenones.The sequential use of soft titanium tetrachloride to perform the Fries rearrangement followed by hard aluminum chloride to achieve the elimination of a protecting tert-butyl group allows the synthesis of some previously unknown 3',6'- and 5',6'-dialkyl-2-hydroxypropiophenones.