Sulfuric Acid → 4,4'-Dinitro-2-hydroxybiphenyl

HRID 260411Notes

Reaction equation

HRID 260411 reaction equation
S(=O)(=O)(O)O.[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[C:11](N)[CH:10]=1)([O-:8])=[O:7].N([O-])=[O:26].[Na+]>O>[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[C:11]([OH:26])[CH:10]=1)([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 932654,4'-Dinitro(1,1'-biphenyl)-2-amineHCID 23668193Sodium Nitrite

Product 1

HCID 142501524,4'-Dinitro-2-hydroxybiphenylYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 15.0 mL water and 11.0 mL concentrated sulfuric acid was added to 13.0 g of 4,4'-dinitro-2-aminobiphenyl, and the resulting mixture was stirred for 2 hours while heating, whereupon 26.5 g of crushed ice was added. On an ice bath, an aqueous solution of 3.51 g of sodium nitrite was added dropwise to the aforementioned mixture; the resulting system was mixed for 10 minutes and subsequently allowed to stand at quiescence for several minutes. The reaction mixture was then added dropwise to a boiling solution that had been prepared by adding 33.4 mL concentrated sulfuric acid to 25 mL of water. Boiling was continued for 5 minutes, after which the mixture was poured into a beaker on an ice bath. The filter cake afforded by suction filtration was purified by column chromatography to give 10.9 g of 4,4'-dinitro-2-hydroxybiphenyl as a yellowish brown powder.

Workup

  1. additionwas added
  2. additionthe resulting system was mixed for 10 minutes
  3. waitto stand at quiescence for several minutes
  4. additionThe reaction mixture was then added dropwise to a boiling solution that
  5. customhad been prepared
  6. waitBoiling was continued for 5 minutes
  7. additionafter which the mixture was poured into a beaker on an ice bath
  8. customThe filter cake afforded by suction filtration
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-37e6034a31e34c1f8856ef546dd89698
Source dataset
uspto-grants-1996_06
Patent number
US05527862

Reaction notes

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