HCID 13577659, compound → HCID 13577665, compound
Reaction equation
[NH2:1][C:2]1[C:7]([CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][C:5]([Cl:16])=[CH:4][C:3]=1[CH2:17][CH2:18][OH:19]>C1C=CC=CC=1.[O-2].[O-2].[Mn+4]>[NH2:1][C:2]1[C:3]([CH2:17][CH2:18][OH:19])=[CH:4][C:5]([Cl:16])=[CH:6][C:7]=1[C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:15]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A suspension of 14 g (0.05 mole) of 2-amino-5-chloro-3-[hydroxy(phenyl)methyl]benzene ethanol in 500 ml of benzene was treated with 23 g (0.25 mole) of activated manganese dioxide and brought to reflux in a vessel fitted with a Dean-Stark trap. After 5 hours the hot mixture was filtered through Celite and the benzene stripped to yield a yellow material. This material was recrystallized from ethanol:pet. ether (30:60) to give 10.8 g of the titled compound, m.p. 135°-137° C.