Methyl Ethyl Ketone → 3,6-Dipropoxybenzene-1,2-dicarbonitrile

HRID 1416804Notes

Reaction equation

HRID 1416804 reaction equation
[CH2:1](I)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[C:11]([C:13]1[C:19]([C:20]#[N:21])=[C:18]([OH:22])[CH:17]=[CH:16][C:14]=1[OH:15])#[N:12].[CH3:23][C:24](=O)[CH2:25]C>>[CH2:1]([O:22][C:18]1[CH:17]=[CH:16][C:14]([O:15][CH2:23][CH2:24][CH3:25])=[C:13]([C:11]#[N:12])[C:19]=1[C:20]#[N:21])[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 784672,3-Dicyanohydroquinone

Product 1

HCID 141504893,6-Dipropoxybenzene-1,2-dicarbonitrile

Procedure

Propyl iodide (15 mL, 0.16 mol) and anhydrous potassium carbonate (24 g, 0.17 mol) are combined with to a solution of 2,3-dicyanohydroquinone (3.0 g, 0.019 mol) in 100 mL of 2-butanone. The reaction mixture is refluxed for 18 hr. under a stream of argon, cooled to room temperature and the solid collected by filtration. The residue is then added to water (100 mL) to dissolve the potassium carbonate and the resulting solid is collected by filtration and dried under vacuum to yield 3.4 g (74%).

Workup

  1. temperatureThe reaction mixture is refluxed for 18 hr
  2. filtrationthe solid collected by filtration
  3. additionThe residue is then added to water (100 mL)
  4. dissolutionto dissolve the potassium carbonate
  5. filtrationthe resulting solid is collected by filtration
  6. customdried under vacuum
  7. customto yield 3.4 g (74%)

Sources & evidence

ORD record
ord-ba3187c309cb4fd09fc0512ad2438e1a
Source dataset
uspto-grants-1999_06
Patent number
US05916481

Reaction notes

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