Nitric Acid → 2-Nitro-4-phenylsulfonylphenol

HRID 2224058Notes

Reaction equation

HRID 2224058 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[N+:22]([O-])([OH:24])=[O:23]>>[C:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[C:14]([N+:22]([O-:24])=[O:23])[CH:15]=2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 3438044-(Benzenesulfonyl)phenol

Product 1

HCID 159333442-Nitro-4-phenylsulfonylphenolYield 112.3%

Procedure

Using the procedure of J. Org. Chem. 59(15) 1994, 4301, 4-benzenesulfonyl-phenol (5.348 g, 22.8 mmol) was added to 3.07 mL of conc. H2SO4 with stirring. Concentrated HNO3 (1.28 g) was added dropwise via addition funnel, and the reaction mixture was stirred under nitrogen for 4 hours. The reaction mixture was then poured over ice, and the resulting suspension was extracted four times with 50 mL of methylene chloride. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to yield an oil which slowly solidified. The solid was washed with 1:1 EtOAc:hexanes to yield 4-benzenesulfonyl-2-nitro-phenol (6.37 g, quantitative) as a crude solid. MS: 235 (M+H)+.

Workup

  1. stirringthe reaction mixture was stirred under nitrogen for 4 hours
  2. additionThe reaction mixture was then poured over ice
  3. extractionthe resulting suspension was extracted four times with 50 mL of methylene chloride
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto yield an oil which
  7. washThe solid was washed with 1:1 EtOAc

Sources & evidence

ORD record
ord-f272e7771e624153b593827e6d2e537b
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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