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

HRID 1886211Notes

Reaction equation

HRID 1886211 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].COCCO>O>[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

5

Reactant 3

HCID 78451,3-ButadieneHCID 80192-MethoxyethanolHCID 123364025-Nitronaphthalene-1,4-dione

Product 1

HCID 108689405-Nitro-1,4,4a,9a-tetrahydroanthraquinoneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture comprising 10 g of the obtained 5-nitro-1,4-naphthoquinone, 3.3 g of 1,3-butadiene and 40 ml of ethylene glycol monomethyl ether was retained in a 100-milliliter autoclave at 50° C. for 6 hours with stirring. The reaction pressure was initially 1.2 atmospheres and 1.0 atmosphere when the reaction was over. Thereafter, 60 ml of water was added to the reaction mixture and cooled to 25° C. The precipitated crystals were filtered, washed with 30 ml of methyl alcohol and dried under reduced pressure to obtain 11.9 g of white 5-nitro-1,4,4a,9a-tetrahydroanthraquinone having a purity of 98%.

Workup

  1. customThe reaction pressure
  2. filtrationThe precipitated crystals were filtered
  3. washwashed with 30 ml of methyl alcohol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-3d5f798d9b73467eabfb870ca63c1b31
Source dataset
uspto-grants-1992_09
Patent number
US05149848

Reaction notes

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