By Robert Martin
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15%) [1069]. p. 134-135° [1069]. wt. 05 Syntheses OH -Preparation by reaction of 48% hydrobromic acid on 2-iodo-4-methoxyacetophenone in acetic acid at 100°, in a sealed tube (45%) [1001]. I -Also obtained (by-product) by reaction of acetyl chloride on COCH3 3-iodoanisole with aluminium chloride in refluxing carbon disulfide (9%) [1001]. -Also obtained in very small quantities by Fries rearrangement of 3-iodophenyl acetate with aluminium chloride in nitrobenzene at 90-95° [385]. p. 131-132° [1001], 128-136° [385].
COMPOUNDS DERIVED FROM ACETIC ACID 49 -Synthesis of 3-hydroxyacetophenone by means of organocadmium derivatives (77%) [1485]. -Preparation by reductive deamination of 2-amino-5-hydroxyacetophenone [682]. -Preparation by aromatization of 5-acetyl-2-cyclohexenone [197] promoted by, *cupric bromide and lithium bromide in refluxing acetonitrile (75%). *Pd/C in refluxing xylene (40%). -Also obtained by treatment of acetophenone with sodium trifluoroacetate in nitromethanetrifluoroacetic acid-trifluoroacetic anhydride mixture in the presence of a platinum electrode, followed by treatment of the intermediate trifluoroester with 10% potassium hydrogen carbonate solution (14%) [1661], (hydroxylation of aromatic compounds).
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]. -Also obtained by Fries rearrangement of 2-iodophenyl acetate with aluminium chloride [370]. p. 174-175° [441], 172-173° [535] [1562], 171-172° [370], 162° [484], 158° [1849]; UV [441]. wt. t. (93%) [1558]. -Preparation by addition of an aqueous iodine and iodic acid solution on resacetophenone in ethanol at ambient temperature (86%) [1600] [1850].