Dimethyl Sulfate → 3,6-Dimethoxyphthalonitrile

HRID 1416803Notes

Reaction equation

HRID 1416803 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[C:8](=O)([O-])[O-].[K+].[K+].[C:14]([C:16]1[C:22]([C:23]#[N:24])=[C:21]([OH:25])[CH:20]=[CH:19][C:17]=1O)#[N:15]>CC(=O)CC>[CH3:8][O:25][C:21]1[CH:20]=[CH:19][C:17]([O:6][CH3:7])=[C:16]([C:14]#[N:15])[C:22]=1[C:23]#[N:24]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 784672,3-Dicyanohydroquinone

Product 1

HCID 3583583,6-Dimethoxyphthalonitrile

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Dimethyl sulfate (15 mL, 0.16 mol) and anhydrous potassium carbonate (24 g, 0.17 mol) are added to a solution of 2,3-dicyanohydroquinone (3.0 g, 0.019 mol) in 100 mL 2-butanone. The reaction mixture is refluxed for 18 hr. under a stream of argon, cooled to room temperature and the resulting solid is collected by filtration. The residue is added to water (100 mL) to dissolve the potassium carbonate and the resulting insoluble material is collected by filtration and dried under vacuum to yield 3.10 g (88%), m.p. 276-280° C., 1H NMR (DMSO-d6) in ppm, δ=7.63 (s, 2 H), 3.93 (s, 6 H).

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hr
  2. filtrationthe resulting solid is collected by filtration
  3. additionThe residue is added to water (100 mL)
  4. dissolutionto dissolve the potassium carbonate
  5. filtrationthe resulting insoluble material is collected by filtration
  6. customdried under vacuum
  7. customto yield 3.10 g (88%), m.p. 276-280° C., 1H NMR (DMSO-d6) in ppm, δ=7.63 (s, 2 H), 3.93 (s, 6 H)

Sources & evidence

ORD record
ord-5f9027da85204de688b2f93536c14750
Source dataset
uspto-grants-1999_06
Patent number
US05916481

Reaction notes

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