4-Cyanobenzaldehyde → 4-(2-Methoxyethenyl)benzonitrile

HRID 375505Notes

Reaction equation

HRID 375505 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:24]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)#[N:25]>COC(C)(C)C>[CH3:2][O:3][CH:4]=[CH:30][C:29]1[CH:32]=[CH:33][C:26]([C:24]#[N:25])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 660424-CyanobenzaldehydeHCID 2723798Methoxymethyl-triphenylphosphonium chloride

Product 1

HCID 536603324-(2-Methoxyethenyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

A suspension of 37.2 g of methoxymethyl-triphenylphosphonium chloride in 250 ml of t-butyl methyl ether is treated at room temperature while gassing with argon with 13.4 g of potassium t-butylate and stirred for 1 hour. Subsequently, the reaction mixture is treated at about 20° C. with a mixture of 9.49 g of 4-cyanobenzaldehyde and 100 ml of t-butyl methyl ether and stirred for a further 1 hour. Thereafter, the reaction mixture is partitioned in diethyl ether/water. The aqueous phase is extracted several times with diethyl ether. The organic phases are washed with water, dried over magnesium sulfate, filtered and evaporated. Chromatographic purification of the resulting crude product on silica gel with petroleum ether and toluene/hexane (vol. 3:1) gives 4-(2-methoxyvinyl)benzonitrile.

Workup

  1. additionis treated at room temperature
  2. stirringstirred for a further 1 hour
  3. customThereafter, the reaction mixture is partitioned in diethyl ether/water
  4. extractionThe aqueous phase is extracted several times with diethyl ether
  5. washThe organic phases are washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customChromatographic purification of the resulting crude product on silica gel with petroleum ether and toluene/hexane (vol. 3:1)

Sources & evidence

ORD record
ord-6df6fd26267442f9a9228c72f2cf3ec4
Source dataset
uspto-grants-1996_01
Patent number
US05486310

Reaction notes

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