Phenol → 4-(Benzotriazol-2-yl)phenol
Reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.[N:11]([O-])=O.[Na+].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>Cl>[N:1]1[N:11]([C:18]2[CH:19]=[CH:20][C:15]([OH:21])=[CH:16][CH:17]=2)[N:6]=[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=12Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
o-Nitroaniline (0.5 mole) was diazotized in the usual manner with concentrated hydrochloric acid (200 ml.) and sodium nitrite (0.5 mole). The clear diazonium solution was added slowly to a cold solution (0-5° C.) of phenol (0.5 mole) in 450 ml. of 10% sodium hydroxide. The mixture was stirred for 1 hour and compound A filtered out (60% yield). One-tenth mole of compound A was dissolved in 100 ml. of 2N NaOH. Zinc dust (30 g.) and sodium hydroxide (50 ml. of a 25% solution) were added slowly to the well-stirred solution to keep the temperature below 45° C. The mixture was then cooled to <30° C. and acidified with concentrated hydrochloric acid. After stirring for 2 hours, the precipitate was filtered. Recrystallization from ethanol-water gave p-(2H-benzotriazol-2-yl)phenol (B) in 90% yield (mp 216°-18° ). ##STR18##
Workup
- filtrationcompound A filtered out (60% yield)
- dissolutionOne-tenth mole of compound A was dissolved in 100 ml
- additionof a 25% solution) were added slowly to the well-stirred solution
- customthe temperature below 45° C
- temperatureThe mixture was then cooled to <30° C.
- stirringAfter stirring for 2 hours
- filtrationthe precipitate was filtered
- customRecrystallization from ethanol-water
Sources & evidence
- ORD record
- ord-7bbe5c9f98f547b18625c8775ac3cf80
- Source dataset
- uspto-grants-1977_12
- Patent number
- US04065427
Reaction notes
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