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

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

Reactant 4

HCID 6569Methyl Ethyl Ketone

HCID 11430Potassium Carbonate

HCID 336431-Iodopropane

HCID 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%).