1,3-Butadiene → 5-Nitro-1,4,4a,9a-tetrahydroanthraquinone

HRID 1731003Notes

Reaction equation

HRID 1731003 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]=[CH:8][C:9]2=[O:14])([O-:3])=[O:2].[CH2:16]=[CH:17][CH:18]=[CH2:19]>C(O)C>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[C:6](=[O:15])[CH:7]1[CH:8]([C:9]2=[O:14])[CH2:19][CH:18]=[CH:17][CH2:16]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 78451,3-ButadieneHCID 123364025-Nitronaphthalene-1,4-dione

Product 1

HCID 108689405-Nitro-1,4,4a,9a-tetrahydroanthraquinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

122 Grams of 5-nitro-1,4-naphthoquinone which contained 10% of the 6-nitro compound, 1,000 grams of ethanol and 48 grams of 1,3-butadiene were placed in an autoclave, followed by reaction at 80° C. for 2.5 hours. After the solution was allowed to cool for precipitating crystals, the crystals were separated by filtration, washed with water and dried to obtain 114 grams of 5-nitro-1,4,4a,9a-tetrahydroanthraquinone. The thus obtained nitro compound was introduced into 2,800 grams of methyl cellosolve, to which was added 1.2 grams of a 5% palladium on carbon catalyst and 120 grams of a 20% aqueous sodium hydroxide solution, followed by feeding hydrogen thereinto for hydrogenation while agitating at room temperature and under normal pressure to absorb hydrogen in an amount of 2 mols per mol of the crude 5-nitro compound. Thereafter, the catalyst was separated by filtration and air was injected to the resultant filtrate for oxidation at room temperature for 3 hours. Then, the methyl cellosolve was distilled off from the reaction solution until crystals were precipitated, followed by allowing to cool. The thus precipitated crystals were separated by filtration, washed with water and dried to obtain 92 grams of 1-aminoanthraquinone containing therein 1% of 2-aminoanthraquinone.

Workup

  1. customfollowed by reaction at 80° C. for 2.5 hours
  2. temperatureto cool
  3. customfor precipitating crystals
  4. customthe crystals were separated by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-0f8e86daa08442bc9f7cd08d29d5ec9b
Source dataset
uspto-grants-1976_11
Patent number
US03994932

Reaction notes

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