Benzaldehyde → Malononitrile, benzylidene-

HRID 2177257Notes

Reaction equation

HRID 2177257 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:13])[CH2:10][C:11]#[N:12].N1CCCCC1>C(O)CCC>[C:2]1([CH:1]=[C:10]([C:9]#[N:13])[C:11]#[N:12])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8010MalononitrileHCID 8082Piperidine

Product 1

HCID 17608Malononitrile, benzylidene-

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
20 °C

Procedure

Into a 50-mL round-bottom flask, was placed benzaldehyde (4 g, 37.69 mmol, 1.00 equiv), propanedinitrile (3.3 g, 49.95 mmol, 1.30 equiv), n-butanol (10 mL), piperidine (1 mL). The resulting solution was stirred for 16 h at 20° C. The resulting mixture was concentrated under vacuum. The resulting mixture was washed with 1×33 mL of H2O/EtOH(10/1). The solids were collected by filtration. The solid was dried in an oven. This resulted in 4.2 g (69%) of 2-(phenylmethylidene)propanedinitrile as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. washThe resulting mixture was washed with 1×33 mL of H2O/EtOH(10/1)
  4. filtrationThe solids were collected by filtration
  5. customThe solid was dried in an oven
  6. customThis resulted in 4.2 g (69%) of 2-(phenylmethylidene)propanedinitrile as a yellow solid

Sources & evidence

ORD record
ord-23aad56206184103b6c8de6248fbbca6
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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