Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[N:10]([O-])=O.[Na+].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=1.[OH-].[Na+]>Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]=[N:10][C:20]2[CH:21]=[C:16]([O:15][CH3:14])[CH:17]=[C:18]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:19]=2[OH:22])=[CH:5][CH:4]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
p-Anisidine (257 g) was dissolved in 514 ml of conc. hydrochloric acid, and under ice-cooling, 1530 ml of an aqueous solution containing 158 g of sodium nitrite was added dropwise to the solution. This mixture was added dropwise under ice-cooling to 3000 ml of an aqueous solution containing 356 g of 4-methoxy-2-tert-butylphenol and 416 g of sodium hydroxide. The resulting mixture was stirred at the same temperature for 15 minutes. Conc. hydrochloric acid (about 400 ml) was added dropwise to the reaction mixture to adjust pH of the mixture to 3, and the precipitated crystals were collected by filtration. The crystals were washed and dried, and recrystallized from a mixed solution of chloroform and ethanol to give 400 g of 2-(4-methoxyphenylazo)-4-methoxy-6-tert-butylphenol (yield: 64%, melting point: 125°-127° C., IR: 1600 cm-1).
Workup
- temperatureunder ice-cooling
- additionwas added dropwise to the solution
- additionThis mixture was added dropwise under ice-
- filtrationthe precipitated crystals were collected by filtration
- washThe crystals were washed
- customdried
- customrecrystallized from a mixed solution of chloroform and ethanol
Sources & evidence
- ORD record
- ord-b437a585c04944d18271f66039854825
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849732
Linked notes
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