(4-Fluorophenyl)[2-hydroxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone → [5-(4-Amino-2,6-dimethylphenoxy)-2-hydroxyphenyl](4-fluorophenyl)methanone
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[C:14]([O:16][C:17]3[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-])=O)=[CH:19][C:18]=3[CH3:27])[CH:13]=[CH:12][C:11]=2[OH:28])=[O:9])=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pt]>[NH2:24][C:20]1[CH:21]=[C:22]([CH3:23])[C:17]([O:16][C:14]2[CH:13]=[CH:12][C:11]([OH:28])=[C:10]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[O:9])[CH:15]=2)=[C:18]([CH3:27])[CH:19]=1Participants
4
Procedure
(4-Fluorophenyl)[2-hydroxy-5-(2,6-dimethyl-4-nitrophenoxy)phenyl]methanone (62.8 g, 0.16 mol) is dissolved in ethyl acetate (4 L) and hydrogenated at atmospheric pressure over 5% platinum on carbon (13.2 g). When the theoretical amount of hydrogen is consumed, the hydrogenation is stopped, the catalyst is filtered off, and the ethyl acetate solution is concentrated to dryness at 50°/3 mm Hg. The residue is triturated hot with isopropanol (1 L) and collected to yield [5-(4-amino-2,6-dimethylphenoxy)-2-hydroxyphenyl](4-fluorophenyl)methanone, m.p. 198°-202°.