By Robert Martin
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Additional resources for Handbook of hydroxyacetophenones : preparation and physical properties [2 vols]
Sample text
Wt. 04 COCH3 HO NO2 -Preparation by nitration of 2,4-dihydroxy-3-iodoacetophenone [928]. -Preparation by iodination of 2,4-dihydroxy-5-nitroacetophenone [928]. p. 189° [928]. wt. t. 5 h (75-85%) [484] or at 60° [1849] [1850], (75%) [1849]. p. 128° [484], 127° [1849], 126° [439], 125°5-126° [440] [443]; UV [443]. wt. t. [438] [440] [441] [442] [1425], (75%) [441] [1425]. 5 h (75-85%) [484] or in 50% aqueous ethanol (61-69%) [370] [1849] [1850]. -Preparation by iodination of 4-hydroxyacetophenone by treatment with iodine monochloride (good yield) [535] [1562].
1H NMR [170] [471], IR [170], UV [170]. wt. 15 COCH3 -Preparation by reaction of acetic anhydride on 4-nitroresorcinol with aluminium chloride in nitrobenzene [1291] [1591], (37%) [1291]. OH -Preparation by Fries rearrangement of 4-nitroresorcinol diacetate with aluminium chloride in nitrobenzene at 95-100° (38%) [49]. -Also obtained by nitration of 2,6-dihydroxyacetophenone (77%) [471], (27%) [1291]. -Also obtained by demethylation of 2,6-dimethoxy-3-nitroacetophenone with aluminium chloride or with boiling 10% aqueous sodium hydroxide (quantitative yield) [1291].
Wt. 05 COCH3 -Preparation from 3-bromo-2-hydroxyacetophenone by persulfate oxidation (Elbs reaction) [743]. -Also obtained by hydrolysis of 8-bromo-6-hydroxy2-methylchromone with a 10% aqueous solution of sodium OH hydroxide, heated on a sand bath [516]. t. [516]. -Also refer to: [667] [668]. : All the results of reference [516] were erroneous [170]. p. 142-144° [743], 132° [516]. wt. 05 COCH3 -Obtained by saponification of 8-acetyl-6-bromo-7-hydroxy4-methylcoumarin with 10% aqueous sodium hydroxide solution at reflux (64%) [1593] [1594].