P-Cresol → 4-Methyl-2-[2-(2-nitrophenyl)diazenyl]phenol

HRID 1792088Notes

Reaction equation

HRID 1792088 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[CH:11]1[C:16]([OH:17])=[CH:15][CH:14]=[C:13]([CH3:18])[CH:12]=1.CCC(COC(C([N:41](CC[NH+](C)C)C)=O)(C1C=CC=CC=1)C1C=CC=CC=1)CC.[Cl-].N(OS(=O)(=O)O)=O>O.S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[N:6]=[N:41][C:11]1[CH:12]=[C:13]([CH3:18])[CH:14]=[CH:15][C:16]=1[OH:17])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 2879P-CresolHCID 69462-NitroanilineHCID 19153X 1002×HCID 82157Nitrosylsulfuric acid

Product 1

HCID 740294-Methyl-2-[2-(2-nitrophenyl)diazenyl]phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of 2-nitroaniline (27.63 g, 0.2 mol), para-cresol (10.81 g, 0.10 mol), Hostapur® SAS93 (1.55), Triton X-100® [polyethylene(10) isooctylphenyl ether] (2.45 g) and water (100 mL) is heated to 50° C. The reaction mixture is rapidly stirred at this temperature for 15 minutes and then the rapidly stirred resultant suspension is allowed to cool to room temperature. The reaction mixture is cooled to 11° C. and a solution of sulfuric acid (11.99 g, 0.12 mol), Hostapur® SAS93 (0.51), and Triton X-100® [polyethylene(10) isooctylphenyl ether] (0.73 g) in 20 mL of water is added dropwise. To the resultant suspension is added dropwise at 9–11° C. nitrosylsulfuric acid (25.40 g, 0.2 mol, 63.51 grams of a 40% solution of nirosylsulfuric acid in sulfuric acid). Upon completion of the reaction, the aqueous phase is separated and the resultant crude product washed by decantation with water (300 mL). An analytical sample is prepared by dry-column flash chromatography (1:1 toluene:heptane eluent)(dry-column flash chromatography method reference: Leonard, J.; Lygro, B.; Procter., G. Advanced Practical Organic Chemistry 2 Ed.; Blackie Academic: London, 1995, pp 215–216).

Workup

  1. stirringthe rapidly stirred resultant suspension
  2. temperatureto cool to room temperature
  3. temperatureThe reaction mixture is cooled to 11° C.
  4. customUpon completion of the reaction
  5. customthe aqueous phase is separated
  6. washthe resultant crude product washed by decantation with water (300 mL)
  7. customAn analytical sample is prepared by dry-column flash chromatography (1:1 toluene:heptane eluent)(dry-column flash chromatography method reference: Leonard, J.; Lygro, B.; Procter., G. Advanced Practical Organic Chemistry 2 Ed.; Blackie Academic: London, 1995, pp 215–216)

Sources & evidence

ORD record
ord-d5c834b6634d45bfba14c26c79f7b31d
Source dataset
uspto-grants-2006_07
Patent number
US07074906B2

Reaction notes

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