1-(4-hydroxy-3-nitrophenyl)propan-1-one

synthetischePreparation by treatment of 4-hydroxypropiophenone with fuming nitric acid or with nitric acid in concentrated sulfuric acid between 2° and 0° (80%) Preparation by Friedel–Crafts acylation of o-nitrophenol with propionyl chloride in nitrobenzene in the presence of aluminium chloride at 55–60° for 2.5 h, then at r.t. overnight Also obtained (poor yield) by Fries rearrangement of 2-nitrophenyl propionate in nitrobenzene with aluminium chloride at 90° for 8 h, then at r.t. overnight Also obtained by reaction of concentrated nitric acid with 2,2′-dihydroxy-5, 5′-dipropionyldiphenyl sulfide (m.p. 103°) in concentrated sulfuric acid at r.t. overnight.