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

HRID 2259337Notes

Reaction equation

HRID 2259337 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].S([O-])([O-])=[O:26].[Na+].[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 24437Sodium SulfiteHCID 932654,4'-Dinitro(1,1'-biphenyl)-2-amine

Product 1

HCID 142501524,4'-Dinitro-2-hydroxybiphenylYield 150.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a beaker, a mixture of 15.0 mL water and 11.0 mL concentrated sulfuric acid was added to 13.0 g 4,4'-dinitro-2-aminobiphenyl, and agitation was carried out for 2 h while heating, whereupon 26.5 g crushed ice were added. An aqueous solution of 3.51 g sodium sulfite was then added dropwise while on an ice bath, and mixing was carried out for 10 min, whereupon the mixture was allowed to stand for a few minutes. A solution produced by adding 33.4 mL concentrated sulfuric acid to 25 mL water was then boiled, and into this was slowly dropped the reaction mixture indicated above. After continuing boiling for 5 min, the solution was poured into a beaker on an ice bath. The product was then suction-filtered, and the filtrate cake was purified using column chromatography to obtain 10.9 g 4,4'-dinitro-2-hydroxybiphenyl (yield 83.9%) in the form of a yellow-brown powder. The boiling point of the product was 220°-222° C.

Workup

  1. temperaturewhile heating, whereupon 26.5 g
  2. customcrushed ice
  3. additionwere added
  4. additionmixing
  5. waitwas carried out for 10 min, whereupon the mixture
  6. waitto stand for a few minutes
  7. customA solution produced
  8. additioninto this was slowly dropped the reaction mixture
  9. customfor 5 min
  10. additionthe solution was poured into a beaker on an ice bath
  11. filtrationThe product was then suction-filtered
  12. customthe filtrate cake was purified

Sources & evidence

ORD record
ord-c2f090a2ef1b4bf488d9120732fc3845
Source dataset
uspto-grants-1995_12
Patent number
US05473041

Reaction notes

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