1,3-Butadiene → 1-Nitronaphthalene

HRID 622321Notes

Reaction equation

HRID 622321 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:19])[CH:7]1[CH:12]([C:13]2=[O:18])CC=CC1)([O-:3])=[O:2].C=CC=C.[N+:24]([C:27]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:28]=1[C:29](=O)[CH:30]=[CH:31][C:32]2=O)([O-:26])=[O:25]>>[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:5]=1[C:6](=[O:19])[CH:7]=[CH:12][C:13]2=[O:18])([O-:3])=[O:2].[N+:24]([C:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][CH:36]=1)([O-:26])=[O:25]

Participants

5

Reactant 3

HCID 78451,3-ButadieneHCID 108689405-Nitro-1,4,4a,9a-tetrahydroanthraquinoneHCID 123364025-Nitronaphthalene-1,4-dione

Product 2

HCID 68491-NitronaphthaleneHCID 123364025-Nitronaphthalene-1,4-dione

Procedure

The starting 5-nitro-1,4,4a,9a-tetrahydroanthraquinone of formula II is known and can be prepared e.g. by Diels-Alder reaction of butadiene with 5-nitro-1,4-naphthoquinone. 5-Nitro-1,4-naphthoquinone can in turn be obtained e.g. by electrolytic oxidation of 1-nitronaphthalene or by nitration of 1,4-naphthoquinone.

Workup

  1. customcan be prepared e.g.

Sources & evidence

ORD record
ord-5205d532e0a246ef93f0e92f5ba5a842
Source dataset
uspto-grants-1988_09
Patent number
US04770818

Reaction notes

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