By Robert Martin
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Additional resources for Handbook of hydroxyacetophenones : preparation and physical properties [2 vols]
Wt. 04 COCH3 HO NO2 -Preparation by nitration of 2,4-dihydroxy-3-iodoacetophenone . -Preparation by iodination of 2,4-dihydroxy-5-nitroacetophenone . p. 189° . wt. t. 5 h (75-85%)  or at 60°  , (75%) . p. 128° , 127° , 126° , 125°5-126°  ; UV . wt. t.     , (75%)  . 5 h (75-85%)  or in 50% aqueous ethanol (61-69%)   . -Preparation by iodination of 4-hydroxyacetophenone by treatment with iodine monochloride (good yield)  .
1H NMR  , IR , UV . wt. 15 COCH3 -Preparation by reaction of acetic anhydride on 4-nitroresorcinol with aluminium chloride in nitrobenzene  , (37%) . OH -Preparation by Fries rearrangement of 4-nitroresorcinol diacetate with aluminium chloride in nitrobenzene at 95-100° (38%) . -Also obtained by nitration of 2,6-dihydroxyacetophenone (77%) , (27%) . -Also obtained by demethylation of 2,6-dimethoxy-3-nitroacetophenone with aluminium chloride or with boiling 10% aqueous sodium hydroxide (quantitative yield) .
Wt. 05 COCH3 -Preparation from 3-bromo-2-hydroxyacetophenone by persulfate oxidation (Elbs reaction) . -Also obtained by hydrolysis of 8-bromo-6-hydroxy2-methylchromone with a 10% aqueous solution of sodium OH hydroxide, heated on a sand bath . t. . -Also refer to:  . : All the results of reference  were erroneous . p. 142-144° , 132° . wt. 05 COCH3 -Obtained by saponification of 8-acetyl-6-bromo-7-hydroxy4-methylcoumarin with 10% aqueous sodium hydroxide solution at reflux (64%)  .