1,3-Butadiene → HCID 21292556, compound

HRID 1077336Notes

Reaction equation

HRID 1077336 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])[C:7]1[CH2:16][CH2:17][CH2:18][CH2:19][C:8]=1[C:9]2=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 2

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

Product 1

HCID 21292556HCID 21292556, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

24.8 g of crude 5-nitronaphthoquinone (comprised of 82 wt% of 5-nitronaphthoquinone and 10 wt% of 6-nitronaphthoquinone), 12.1 g of 1,3-butadiene, and 124 g of ethanol were introduced into an autoclave. The autoclave was hermetically sealed and the reaction was effected at about 80°C for 2.5 hours. The resultant reaction solution was cooled to 25°-30°C to crystalize 5-nitrotetrahydroanthraquinone, and filtered. The cake was washed with 40 g of ethanol and dried to obtain 22.9 g of 5-nitrotetrahydroanthraquinone. The yield was 89.0%.

Workup

  1. customThe autoclave was hermetically sealed
  2. customThe resultant reaction solution
  3. temperaturewas cooled to 25°-30°C
  4. customto crystalize 5-nitrotetrahydroanthraquinone
  5. filtrationfiltered
  6. washThe cake was washed with 40 g of ethanol
  7. customdried

Sources & evidence

ORD record
ord-5332c618108e4c3ab5370489a08169ee
Source dataset
uspto-grants-1976_05
Patent number
US03959318

Reaction notes

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