Water → 3-(3,4-Dimethoxyphenyl)acrylonitrile

HRID 1624855Notes

Reaction equation

HRID 1624855 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.CCOP(OCC)([CH2:18][C:19]#[N:20])=O.CC(C)([O-])C.[K+].O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:6]=[CH:18]/[C:19]#[N:20])[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8419VeratraldehydeHCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 15509583-(3,4-Dimethoxyphenyl)acrylonitrileYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7 g of 3,4-dimethoxybenzaldehyde (42.1 mmoles) are dissolved in 84 mL of THF and the solution is cooled to 0° C. 8.2 g of diethyl cyanomethyl phosphonate (7.5 mL, 46.3 mmoles, 1.1 eq.) and subsequently 5.2 g of potassium tert-butoxide (46.3 mmoles, 1.1 eq.) are added little by little. The mixture is stirred for one hour at 0° C. and then overnight at ambient temperature. The reaction mixture is hydrolysed using 175 mL of water and extracted twice with dichloromethane. The organic phases are collected and the solvent is evaporated off under reduced pressure to yield 7.69 g of the title product in the form of a beige solid.

Workup

  1. customovernight
  2. customat ambient temperature
  3. extractionextracted twice with dichloromethane
  4. customThe organic phases are collected
  5. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b897f1ce897a4b85a57664f67d776c25
Source dataset
uspto-grants-2014_07
Patent number
US08779121B2

Reaction notes

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