1,2,4-Trichlorobenzene → 2-hydroxy-N-(2-methylphenyl)benzamide

反応式

C1(O)C=CC=CC=1.[C:8]([O:17]C1C=CC=CC=1)(=O)[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11].[NH2:24][C:25]1[C:26]([CH3:31])=[CH:27][CH:28]=[CH:29][CH:30]=1.ClC1C=CC(Cl)=CC=1Cl>>[CH3:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:8](=[O:17])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11]

参加物

反応物 4

HCID 131,2,4-Trichlorobenzene

HCID 996Phenol

HCID 7242O-Toluidine

HCID 8361Phenyl Salicylate

生成物 1

HCID 7683182-hydroxy-N-(2-methylphenyl)benzamide収率 90.2%

実験手順

Phenol was distilled from a boiling mixture of phenyl salicylate (42.8 gm, 0.20 mol), 2-toluidine (26.7 gm, 0.25 mol), and 1,2,4-trichlorobenzene (41 mL) as described in the literature procedure (Organic Syntheses, Coll. Vol. 3, 765). The cooled product mixture was transferred to an 250 mL Erlenmeyer flask and boiled with hexanes (75 mL) for 30 minutes. The solid product was isolated from the hot mixture by vacuum filtration. The solid was washed with more hexanes until the filtrate was colorless. Drying gave the pure 2′-methyl-salicylanilide (41 gm, 90%) as an off-white solid.