2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-Acetyloxy-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

HRID 2213161Notes

Reaction equation

HRID 2213161 reaction equation
[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)(=[O:3])[CH3:2].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1.CO>[C:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 129722061-Acetyloxy-2-(3-Methoxyphenyl)-6-Methoxy-3,4-Dihydronaphthalene

Product 1

HCID 129722071-Acetyloxy-2-(3-Methoxyphenyl)-6-Methoxynaphthalene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution was prepared of 52.7 g (162 mmol) of 1-acetyloxy-2-(3-methoxyphenyl)-6-methoxy-3,4-dihydronaphthalene and 36.9 g (162 mmol) of DDQ in 500 mL of p-dioxane. The solution was heated to reflux for two hours under a nitrogen atmosphere. The reaction was allowed to cool and the solvent removed by evaporation. The residue was extracted by stirring in CHCl3 for sixteen hours, then filtering to remove the insoluble material. The CHCl3 extract was further purified by chromatography on a silica gel column eluted with CHCl3. This resulted in a red oil, which was suspended in MeOH and crystallized at −70° C. This yielded 46.5 g of the title compound as a low melting solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for two hours under a nitrogen atmosphere
  3. temperatureto cool
  4. customthe solvent removed by evaporation
  5. extractionThe residue was extracted
  6. filtrationfiltering
  7. customto remove the insoluble material
  8. extractionThe CHCl3 extract
  9. customwas further purified by chromatography on a silica gel column
  10. washeluted with CHCl3
  11. customThis resulted in a red oil, which
  12. customcrystallized at −70° C

Sources & evidence

ORD record
ord-d68dda235f0d418d984e0b69b3ef3020
Source dataset
uspto-grants-2006_09
Patent number
US07105541B2

Reaction notes

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