4-Methoxyphenol → 1,2-Benzenedicarbonitrile, 4-(4-methoxyphenoxy)-

HRID 2253208Notes

Reaction equation

HRID 2253208 reaction equation
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:4]2[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=2)[C:8]#[N:9])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

Product 1

HCID 9520851,2-Benzenedicarbonitrile, 4-(4-methoxyphenoxy)-Yield 106.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-nitro-phthalonitrile (4.00 g), 4-methoxy-phenol (3.46 g) and potassium carbonate (6.39 g) in acetone (64 ml) was heated to reflux for 2 h. Reaction mixture was cooled and filtered. Filtrate was concentrated and the residue was dissolved in ethyl acetate (100 ml). The solution was washed with NaOH (1 N, 50 ml), water, and then brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give the product (6.14 g). 1H NMR (200 MHz, CDCl3) δ 6.70 (d, J=7.8 Hz, 1H), 7.21 (m, 2H), 6.96 (m, 4H), 3.84 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. customReaction mixture
  4. temperaturewas cooled
  5. filtrationfiltered
  6. concentrationFiltrate was concentrated
  7. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  8. washThe solution was washed with NaOH (1 N, 50 ml), water
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-9f7addb9dada4491b12692cc89f292d1
Source dataset
uspto-grants-2008_01
Patent number
US07323475B2

Reaction notes

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