7-Methyl-9,10-dihydroacephenanthrene → 7-Methylacephenanthrylene

HRID 36631

Reaction equation

HRID 36631 reaction equation
[CH3:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:17]4[C:8](=[CH:9][CH:10]=[CH:11][C:12]=4[C:13]=2[CH2:14][CH2:15][CH:16]=1)[CH2:7][CH2:6]3>O1CCOCC1.C(OCC)(=O)C.O>[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:3]=1[CH:4]=[C:5]1[C:17]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]2=3)[CH:7]=[CH:6]1

Participants

5

Reactant 1

HCID 233640227-Methyl-9,10-dihydroacephenanthrene

Product 1

HCID 149320397-MethylacephenanthryleneYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 7-methyl-9,10-dihydroacephenanthrene (0.13 g, 0.59 mmol) and dichlorodicyanoquinone (0.27 g, 1.18 mmol) in dioxane (10 ml) was heated at reflux for 0.5 h. The reaction mixture was allowed to cool and was diluted with ethyl acetate (50 mL) and water (20 mL). The organic layer was separated, washed with water (3×20 mL) and brine solution (3×20 mL), dried (MgSO4), and concentrated under reduced pressure. The resulting solid was purified by flash chromatography to give 0.07 g (57%) of the product: 1H NMR (CDCl3, 300 MHz) δ 8.54 (d, 1H, J=8.0 Hz), 8.40 (dd, 1H, J=7.3, 6.9 Hz), 8.24 (s, 1H), 7.66 (m, 2H), 7.58 (dd, 1H, J=8.4, 7.3 Hz), 7.46 (d, 1H, J=7.3 Hz), 7.20 (d, 1H, J= 5.1 Hz), 7.16 (d, 1H, J=5.4 Hz), 2.82 (s, 3H).

Workup

  1. temperatureat reflux for 0.5 h
  2. temperatureto cool
  3. customThe organic layer was separated
  4. washwashed with water (3×20 mL) and brine solution (3×20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting solid was purified by flash chromatography

Sources & evidence

ORD record
ord-bce723b98280443fb7ed47abb8f261cf
Source dataset
uspto-grants-1995_05
Patent number
US05416089

Linked notes

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