1,4-Naphthoquinone → 1,4-Naphthoquinone

HRID 1973704Notes

Reaction equation

HRID 1973704 reaction equation
[C:1]1(=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH:3]=[CH:2]1.[C:13]([O:16][CH:17]=[CH:18][CH:19]=[CH2:20])(=[O:15])[CH3:14]>C(O)(=O)C>[C:4]1(=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1](=[O:12])[CH:2]=[CH:3]1.[C:13]([O:16][CH:17]=[CH:18][CH:19]=[CH2:20])(=[O:15])[CH3:14].[C:13]([O:16][CH:17]1[CH:2]2[CH:3]([C:4](=[O:11])[C:5]3[C:10]([C:1]2=[O:12])=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:20][CH:19]=[CH:18]1)(=[O:15])[CH3:14]

Participants

6

Reactant 2

HCID 85301,4-Naphthoquinone2×HCID 151951,3-Butadienyl acetate2×

Product 3

HCID 85301,4-NaphthoquinoneHCID 151951,3-Butadienyl acetateHCID 12400982HCID 12400982, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

It is known from German Pat. No. 739,438, to obtain anthraquinone by reaction of 1,4-naphthoquinone with excess 1-acetoxybutadiene at the reflux temperature. However, the yield is only 57% of theory. Furthermore it is known, from Liebig's Ann. Chem. volume 568 (1950), page 28, to warm 1,4-naphthoquinone with excess 1-acetoxybutadiene in acetic acid, separate off the resulting anthraquinone (19% of theory), isolate from the reaction solution the addition product first formed from 1,4-naphthoquinone and 1-acetoxybutadiene, namely 1-acetoxy-1,4,4a,9a-tetrahydroanthraquinone, and convert this into anthraquinone by means of methanolic potassium hydroxide solution in the presence of air. While this process gives a total yield of anthraquinone of about 80% of theory, it is unsuitable for large scale industrial use.

Workup

  1. customseparate off the resulting anthraquinone (19% of theory)
  2. customisolate from the reaction solution the addition product

Sources & evidence

ORD record
ord-88180a27738141e485d53b161e01c4fd
Source dataset
uspto-grants-1976_12
Patent number
US03998857

Reaction notes

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