2',5'-DIHYDROXYPROPIOPHENONE

Chemical properties

yellowish crystalline powder

Preparation

Preparation by Fries rearrangement of quinol dipropionate (hydroquinone dipropionate),
with aluminium chloride without solvent at 130–140° for 4 h (75%), ? at 142° for 30 min (80%), at 160–165° for 3 h (good yields) or at 190–200° for 90 min (60%)
by using various quantities of aluminium chloride at 180° for 2 h (to see ? below)
with aluminium chloride (2 equiv) in nitromethane at 20° for a week (7%) ? or in nitrobenzene (24%)
with boron trifluoride complex (BF? 3-OBu2) at reflux for 1 h (42%)
by using titanium tetrachloride (2 equiv) at 130° for 2 h gave only 6% yield
Also obtained by treatment of
hydroquinone dipropionate with aluminium chloride in the presence of hyd-? roquinone (61%)
2-hydroxy-5-(propionyloxy)propiophenone with aluminium chloride (5 equiv) ? at 180° for 30 min in the presence of hydroquinone (57%)
Also obtained by acylation of hydroquinone with propionic acid
in the presence of boron trifluoride in ethylene dichloride at 50–55° (59%) ?, in tetrachloroethane at 90–95° for 5 h (70%) or at 50° for 4 h (70%) or without solvent (67%) at 80° for 2 h (54%) or at 125° for 2 h (71%)
in the presence of zinc chloride at 190° few min (Nencki reaction)
in the presence of 70% perchloric acid at reflux for 1 h (12%)
Also obtained by Friedel–Crafts acylation of hydroquinone with propionyl chlo-ride in nitrobenzene in the presence of aluminium chloride (40%)
Also obtained from 2-hydroxy-5-(propionyloxy)propiophenone; the ester group elimination on hydrolysis with 85% sulfuric acid at r.t. or by treatment with by aluminium chloride
Also obtained by reaction of benzoquinone (2.5 equiv) with 2-oxobutanoic acid in aqueous acetonitrile or an acetonitrile/methylene chloride mixture (91%).