Benzaldehyde, 3,5-dimethyl- → 3-(3,5-Dimethyl-phenyl)-acrylonitrile

HRID 426166

Reaction equation

HRID 426166 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:10])[CH:9]=1)[CH:5]=O.[C:11]([CH2:13]P(=O)(OCC)OCC)#[N:12].CC(C)([O-])C.[K+]>C1COCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:13][C:11]#[N:12])[CH:7]=[C:8]([CH3:10])[CH:9]=1

Participants

5

Reactant 3

HCID 34225Benzaldehyde, 3,5-dimethyl-HCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 667054533-(3,5-Dimethyl-phenyl)-acrylonitrileYield 94.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 3,5-dimethyl benzaldehyde (13.4 g, 0.1M), diethyl cyanomethylphosphonate (19.4 g, 0.11M) in anhydrous THF (200 ml) under nitrogen at 0° C. (ice bath), was added potassium t-butoxide (12.3 g, 0.11M). After stirring for 1 hr., the mixture was stirred for overnight at room temperature. The mixture was then partitioned between ether and water. The ether layer was taken, dried with anhydrous magnesium sulfate, filtered, evaporated in vacuo, and the residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:20)) to afford 14.8 g (86%) of a white solid. m.p. 67-68° C.; 1H NMR (200 MHz, CDCl3) δ 2.33 (6H, s), 5.83 (1H, d, J=16.6 Hz), 7.05 (3H, s), 7.28 (1H, d, J=16.6 Hz).

Workup

  1. stirring, the mixture was stirred for overnight at room temperature
  2. customThe mixture was then partitioned between ether and water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customthe residue was purified by silica gel column chromatography (eluent, ether:hexanes (1:20))

Sources & evidence

ORD record
ord-54ef9bf61005419483207af4c5d88c10
Source dataset
uspto-grants-2012_01
Patent number
US08106064B2

Linked notes

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