Methanol → Anthraquinone

HRID 2052444Notes

Reaction equation

HRID 2052444 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])(O)=[O:16].[CH3:19][OH:20]>>[CH:6]1[C:7]2[C:19](=[O:20])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:1](=[O:16])[C:2]=2[CH:3]=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 944Nitric Acid2×HCID 697382-Benzyltoluene

Product 1

HCID 6780Anthraquinone

Procedure

A process for the manufacture of anthraquinones in which o-benzyl-toluene is first oxidized with 25 to 50 weight-% nitric acid at atmospheric pressure and moderate temperatures, and then further oxidized with a more dilute nitric acid at elevated temperatures and pressures to yield crude o-benzoyl-benzoic acid. The crude product is then esterified with methanol, the methyl ester distilled and, when necessary, recrystallized, and heated with concentrated sulfuric acid to yield anthraquinone in high yield and of a high degree of purity.

Workup

  1. customto yield crude o-benzoyl-benzoic acid
  2. distillationthe methyl ester distilled
  3. customwhen necessary, recrystallized
  4. temperatureheated with concentrated sulfuric acid

Sources & evidence

ORD record
ord-b66a195315014fe2b020edf872f2b465
Source dataset
uspto-grants-1980_01
Patent number
US04185024

Reaction notes

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