Hydrochloric Acid → 26029-68-5

HRID 1636034Notes

Reaction equation

HRID 1636034 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Cl.[N:11]([O-])=O.[Na+].[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[K+]>O>[OH:21][C:15]1[CH:20]=[CH:19][C:18]([N:11]=[N:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 996PhenolHCID 133964-AminobenzonitrileHCID 14797Potassium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 500440126029-68-5Yield 65.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

While stirring 2 mol (236.3 g) of 4-aminobenzonitrile, 600 ml of 12N HCl and 600 ml of purified water in an ice bath, an aqueous solution of NaNO2 (NaNO2 150 g, in 750 ml of purified water) was dropped (Step 1). 2 mol (191.8 g) of phenol and 2 mol (112.3 g) of KOH were rapidly dissolved in about 2 liter of purified water, to which the product in Step 1 was dropped. After filtration under suction, the product was washed with purified water and then dried under a reduced pressure. The product was recrystallized in methanol to obtain 1.3 mol of 4-hydroxy-4′-cyanoazobenzene (292.3 g; yield 65.5%).

Workup

  1. additionwas dropped
  2. filtrationAfter filtration under suction
  3. washthe product was washed with purified water
  4. customdried under a reduced pressure
  5. customThe product was recrystallized in methanol

Sources & evidence

ORD record
ord-7208c00d497f4159b9fe34ae973da3ac
Source dataset
uspto-grants-2003_01
Patent number
US06512085B1

Reaction notes

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