Water → 2-Isopropyl-4-nitrophenol

HRID 1910758Notes

Reaction equation

HRID 1910758 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1N)([CH3:3])[CH3:2].N([O-])=[O:15].[Na+].O>S(=O)(=O)(O)O>[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:15])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 223794772-Isopropyl-4-nitroanilineHCID 23668193Sodium Nitrite

Product 1

HCID 5289542-Isopropyl-4-nitrophenolYield 80%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-Isopropyl-4-nitro-phenylamine (2.5 g, 13.9 mmol) was dissolved in 10% sulfuric acid (25 mL) and to this was added sodium nitrite (1.64 g, 23.8 mmol) in portions over 15 min at 0° C. The diazotized solution was added to boiling water and stirred for 15 min. the mixture was cooled to r.t. and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford 2-isopropyl-4-nitro phenol (2 g, 80%) as a solid.

Workup

  1. additionThe diazotized solution was added
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4eb7d131ed414119bad0b62fa06a9051
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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