Chloroprene → 2-Chloro-1,4,4a,12a-tetrahydrotetracene-5,6,11,12-tetrone

HRID 261157

Reaction equation

HRID 261157 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:9]3[C:17](=[O:18])[CH:16]=[CH:15][C:13](=[O:14])[C:10]=3[C:11](=[O:12])[C:4]2=[CH:3][CH:2]=1)=[O:8].[CH2:19]=[CH:20][C:21]([Cl:23])=[CH2:22]>C(O)(=O)C.CCOCC>[Cl:23][C:21]1[CH2:22][CH:16]2[CH:15]([C:13](=[O:14])[C:10]3[C:11](=[O:12])[C:4]4[CH:3]=[CH:2][CH:1]=[CH:6][C:5]=4[C:7](=[O:8])[C:9]=3[C:17]2=[O:18])[CH2:19][CH:20]=1

Participants

5

Reactant 2

HCID 31369ChloropreneHCID 1371691,4,9,10-Anthradiquinone

Product 1

HCID 203952152-Chloro-1,4,4a,12a-tetrahydrotetracene-5,6,11,12-tetroneYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Quinizarinquinone (I) (1.0 g, 4.2 mmol) and chloroprene (1.12 g, 12.6 mmol) were dissolved in acetic acid (6 ml, glacial) and stirred at ambient temperature under nitrogen for 2.5 days. The reaction mixture was then diluted with ether (25 ml), the reaction mixture filtered, the retained precipitate washed with ether and dried under reduced pressure in the presence of phosphorus pentoxide to yield 9-chloro-6a,7,10,10atetrahydro-5,6,11,12-naphthacenetetraone (II) (988 mg, 72%). Recrystalization (chloroform-ether) gave the foregoing compound in analytical purity m.p. 221°-222° C.,

Workup

  1. filtrationthe reaction mixture filtered
  2. washthe retained precipitate washed with ether
  3. dry with materialdried under reduced pressure in the presence of phosphorus pentoxide

Sources & evidence

ORD record
ord-5bde6b4aee144e2193ad5df9b73ef4be
Source dataset
uspto-grants-1979_08
Patent number
US04164503

Linked notes

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