Phenol → 4-[2-(4-Methoxyphenyl)diazenyl]phenol

HRID 327277Notes

Reaction equation

HRID 327277 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[N:10]([O-])=O.[Na+].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>Cl.O>[OH:20][C:14]1[CH:19]=[CH:18][C:17]([N:10]=[N:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 996PhenolHCID 7732P-AnisidineHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 947994-[2-(4-Methoxyphenyl)diazenyl]phenolYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent3×

Procedure

0.1 moles of p-methoxy aniline was dissolved in 28 ml of concentrated hydrochloric acid and 28 ml of water was added. Then 0.1 moles of sodium nitrite was dissolved in 350 ml of water and the solution was dropped slowly at 0-5° c into the aforementioned solution. 10 g of phenol, 4 g of sodium hydroxide and 21 g of sodium carbonate were dissolved in 350 ml of water and then added dropwisely into the above cold mixed solution at 0-5° C. After 15 minutes, hydrochloric acid with a pH at 2-3 was added and the precipitate was washed twice with 50 ml of water. Compound 4, 4-hydroxyl-4'-methoxyazobenzene, was obtained with a yield of 82% after filtration and recrystallization with chloroform.

Workup

  1. additionthe solution was dropped slowly at 0-5° c into the aforementioned solution
  2. additionadded dropwisely into the above cold mixed solution at 0-5° C
  3. washthe precipitate was washed twice with 50 ml of water

Sources & evidence

ORD record
ord-a8ef77da3c3b48a7aa1c42d4c4e33cd1
Source dataset
uspto-grants-1993_12
Patent number
US05272234

Reaction notes

Loading…