2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenol

HRID 1992852Notes

Reaction equation

HRID 1992852 reaction equation
C([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]=[C:7]([CH2:17][CH3:18])[C:6]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=O)C.C[O-].[Na+].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CO.C1COCC1>[CH2:17]([C:7]1[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:5]([OH:4])[C:14]2[C:9]([CH:8]=1)=[CH:10][C:11]([O:15][CH3:16])=[CH:12][CH:13]=2)[CH3:18]

Participants

6

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 10942334Sodium MethoxideHCID 685362503-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetate

Product 1

HCID 685377153-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenolYield 98.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl acetate (56) (0.61 g, 1.90 mmol) in MeOH (20 mL) and THF (20 mL) was added NaOMe (0.5M in MeOH, 10 mL). The mixture was stirred at room temperature for 3 h. Cooled to room temperature, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.74 g, 7.50 mmol) was added. Most of the solvent was removed and the residue was diluted with water (20 mL) and acidified with 5 N HCl. The mixture was extracted with CH2Cl2. The extracts were combined and washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a brown oil. The crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (10:1) to give 0.52 g (98%) of compound 57 as a light yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.08 (t, J=7.5 Hz, 3H), 2.49 (q, J=7.5 Hz, 2H), 3.93 (s, 3H), 5.14 (s, 1H), 7.05-7.10 (m, 2H), 7.24 (s, 1H), 7.32-7.38 (m, 2H), 7.42-7.48 (m, 1H), 7.50-7.56 (m, 2H), 8.05-8.10 (m, 1H).

Workup

  1. temperatureCooled to room temperature
  2. customMost of the solvent was removed
  3. additionthe residue was diluted with water (20 mL)
  4. extractionThe mixture was extracted with CH2Cl2
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customto give the crude product as a brown oil
  10. customThe crude product was purified by flash chromatography over SiO2 with hexanes:EtOAc (10:1)

Sources & evidence

ORD record
ord-edf18ed0eec346cc90e30826d1eab70b
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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