Hydrochloric Acid → HCID 135537636, compound

HRID 1955369Notes

Reaction equation

HRID 1955369 reaction equation
[N:1]([O-])=O.[Na+].Cl.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[OH:21].[OH-].[Na+]>O>[Cl:20][C:19]1[C:14]([Cl:13])=[C:15]([OH:21])[CH:16]=[CH:17][C:18]=1[N:1]=[N:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric Acid2×HCID 6115AnilineHCID 113342,3-DichlorophenolHCID 14798Sodium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 135537636HCID 135537636, compoundYield 119.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

At 0 to 5° C., a solution of 7.6 g (0.11 mol) of NaNO2 in 12 ml of H2O is added dropwise to 50 ml of aqueous HCl (15%) and 9.8 g (0.105 mol) of aniline in a 100 ml two-neck flask fitted with internal thermometer and magnetic stirrer. After 10 minutes, this diazonium salt solution is added at 5 to 10° C. to a solution of 16.3 g (0.1 mol) of 2,3-dichlorophenol and 20 g (0.5 mol) of NaOH in 200 ml of H2O. The mixture is allowed to warm to room temperature, stirred for an additional 4 hours, neutralized with aqueous HCl and extracted 3× with 100 ml of ethyl acetate each. The combined organic phases are washed with NaCl solution and dried with Na2SO4, and the solvent is distilled off using a rotary evaporator. 31.8 g of (2,3-dichloro-4-hydroxyphenyl)phenyldiazene are obtained.

Workup

  1. customfitted with internal thermometer and magnetic stirrer
  2. extractionextracted 3× with 100 ml of ethyl acetate each
  3. washThe combined organic phases are washed with NaCl solution
  4. dry with materialdried with Na2SO4
  5. distillationthe solvent is distilled off
  6. customa rotary evaporator

Sources & evidence

ORD record
ord-1484f066740445908ac011b116a1580e
Source dataset
uspto-grants-2000_09
Patent number
US06124504

Reaction notes

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