Sulfuric Acid → 1-Nitroanthraquinone

HRID 262071Notes

Reaction equation

HRID 262071 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>O>[N+:18]([C:14]1[C:10]2[C:11](=[O:13])[C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:1](=[O:8])[C:9]=2[CH:17]=[CH:16][CH:15]=1)([O-:20])=[O:19]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 5695322-Benzoyl-6-nitrobenzoic acid

Product 1

HCID 67041-NitroanthraquinoneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-benzoyl-6-nitrobenzoic acid (2.0 grams; 0.0074 mole) in 10 mls. of concentrated sulfuric acid (99.5% by weight) was stirred at 100° C. for 3 hours, then cooled to room temperature and poured into a mixture of ice and water. The resulting mixture was filtered to recover the precipitated solids. The filter cake was then washed successively with a dilute aqueous solution of sodium carbonate and water, and dried to obtain 1-nitroanthraquinone (1.59 grams; 85% yield). The product was identified by comparison of its vapor phase chromatographic spectrum with that of an authentic sample.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customto recover the precipitated solids
  3. washThe filter cake was then washed successively with a dilute aqueous solution of sodium carbonate and water
  4. customdried

Sources & evidence

ORD record
ord-33ee7cb8282a4b66b7d0b8592174087c
Source dataset
uspto-grants-1979_05
Patent number
US04153632

Reaction notes

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