Hydrochloric Acid → HCID 21982878, compound

HRID 1582849Notes

Reaction equation

HRID 1582849 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Mg].[Cl:10][C:11]1[CH:24]=[CH:23][C:22]2[C:21](=O)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=O)[C:13]=2[CH:12]=1.Cl.O.O.Cl[Sn]Cl>C1COCC1.C(O)(=O)C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]2[C:15]3[C:20]([C:21]([C:2]4[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=4)=[C:22]4[C:13]=2[CH:12]=[C:11]([Cl:10])[CH:24]=[CH:23]4)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:3][CH:4]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 78054-BromotolueneHCID 85532-ChloroanthraquinoneHCID 61436Stannous chloride dihydrateHCID 5462224Magnesium

Product 1

HCID 21982878HCID 21982878, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

213.8 g of 4-bromotoluene dissolved in anhydrous THF(200 ml) was slowly added to 32.6 g of magnesium in 500 ml of anhydrous THF for 2 hours. The mixed solution was refluxed for 3 hours, and then cooled to room temperature. 121 g of 2-chloroanthraquinone was added to cooled solution. The resulting solution was stirred for 3 hours, and then refluxed for 3 hours. Then, 400 ml of 10% aqueous hydrochloric acid solution was added to the resulting solution. An organic layer was separated from the solution. The resulting solvent was distilled under a vacuum, by which a brown solution was obtained. 500 ml of Glacial acetic acid and 100 g of SnCl2.2H2O were added to the brown solution. The mixed solution was stirred at room temperature for 1 hour, heated for 3 hours and refluxed. The solution was further stirred at room temperature for 3 hours. Thus, a pale yellow product was obtained. This product was recrystallized using glacial acetic acid. In this way, a pure product was obtained in the form of pale yellow crystals(153 g, m.p. 202-203.5° C., yield 78%). Results of 1H NMR(200 MHz, CDCl3) and IR(KBr) for the obtained compound are described in the following Table 1.

Workup

  1. temperatureThe mixed solution was refluxed for 3 hours
  2. temperatureto cooled solution
  3. temperaturerefluxed for 3 hours
  4. customAn organic layer was separated from the solution
  5. distillationThe resulting solvent was distilled under a vacuum, by which a brown solution
  6. customwas obtained
  7. stirringThe mixed solution was stirred at room temperature for 1 hour
  8. temperatureheated for 3 hours
  9. temperaturerefluxed
  10. stirringThe solution was further stirred at room temperature for 3 hours
  11. customThus, a pale yellow product was obtained
  12. customThis product was recrystallized

Sources & evidence

ORD record
ord-4f1c0bf3284841d19b111c5de4e38287
Source dataset
uspto-grants-2004_05
Patent number
US06740263B2

Reaction notes

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