2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → [6-Methoxy-2-(3-methoxyphenyl)-1-naphthalenyl](4-methoxyphenyl)methanone

HRID 619086Notes

Reaction equation

HRID 619086 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:14])=[C:8]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)[CH2:7][CH2:6]2.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([C:13]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)=[O:14])=[C:8]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 15434589[2-(3-Methoxyphenyl)-3,4-dihydro-6-methoxynaphthalen-1-yl][4-methoxyphenyl]methanone

Product 1

HCID 18182643[6-Methoxy-2-(3-methoxyphenyl)-1-naphthalenyl](4-methoxyphenyl)methanoneYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of [3,4-dihydro-6-methoxy-2-(3-methoxyphenyl)-1-naphthalenyl](4-methoxyphenyl)methanone (14.0 g, 35.0 mmol) was dissolved in anhydrous dioxane (400 mL) under an atmosphere of nitrogen. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 7.0 g, 31 mmol) was added and the solution was refluxed for 16 hours. The reaction mixture was allowed to cool to ambient temperature and the solid dihydroquinone byproduct (8.8 gm) was removed by filtration and discarded. The filtrate was concentrated to dryness and the residue was purified by silica gel chromatography with chloroform as the isocratic elution solvent. Appropriate fractions gave 13.1 g, (94%) of the desired product as an oil. Although the oil contained some minor impurities, it was used without additional purification. 1H NMR (CDCl3) δ 7.88 (d, J=8.6 Hz, 1H), 7.71-7.54 (m, 4H), 7.21 (d, J=2.6 Hz, 1H), 7.18-7.05 (m, 2H), 6.99-6.89 (m, 2H), 6.78-6.70 (m, 3H), 3.94 (s, 3H), 3.78 (s,3H), 3.69 (s,3H); MS (FD) m/e 398 (M+); Anal. Calcd. for C26H22O4 : C, 78.37; H, 5.57. Found: C, 78.22; H, 5.83.

Workup

  1. temperaturethe solution was refluxed for 16 hours
  2. customthe solid dihydroquinone byproduct (8.8 gm) was removed by filtration
  3. concentrationThe filtrate was concentrated to dryness
  4. customthe residue was purified by silica gel chromatography with chloroform as the isocratic elution solvent

Sources & evidence

ORD record
ord-154c9704d67b41c699856357a74fc72f
Source dataset
uspto-grants-1999_09
Patent number
US05958916

Reaction notes

Loading…