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ChemicalBook CAS DataBase List 1-(4-CHLORO-2-HYDROXYPHENYL)PROPAN-1-ONE
1127-97-5

1-(4-CHLORO-2-HYDROXYPHENYL)PROPAN-1-ONE synthesis

6synthesis methods
Preparation by Fries rearrangement of m-chlo- rophenyl propionate (b.p.0.8 90°) with aluminium chloride,
without solvent at 100° for 2 h (92%), at 140° for 2 h (89%), ? at 140–150° for 3 h, at 130° for 2 h (77%), at 165° for 1 h (72%), at 50° for 3 h (55%) or at 30–40° (53%)
n nitrobenzene at 25° for 6 h (87%)
Preparation by Fries rearrangement of m-chlorophenyl propionate with titanium tetrachloride at 100° for 2 h (75%)
Also obtained by Friedel–Crafts reaction of propionyl chloride with m-chlorophenol in the presence of aluminium chloride
Also obtained by isomerization of 2-chloro-4-hydroxypropiophenone on heating with aluminium chloride between 165° and 200° (30–70%).
-

Yield:1127-97-5 89.2%

Reaction Conditions:

with aluminium trichloride at 140; for 2 h;

References:

Shiozawa;Narita;Izumi;Kurashige;Sakitama;Ishikawa [European Journal of Medicinal Chemistry,1995,vol. 30,# 1,p. 85 - 94]