Acetic Acid → 2-(2-Methylbenzylidene)malononitrile

HRID 48307Notes

Reaction equation

HRID 48307 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10](#[N:14])[CH2:11][C:12]#[N:13].C([O-])(=O)C.[NH4+].C(O)(=O)C>C(O)(C)C.O>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:11]([C:10]#[N:14])[C:12]#[N:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8010MalononitrileHCID 107222-MethylbenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 37654742-(2-Methylbenzylidene)malononitrileYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of 2-methylbenzaldehyde (9.6 mL, 83 mmol), malononitrile (5.5 g, 83 mmol) and 3.5 M ammonium acetate in acetic acid (2.4 mL, 8.4 mmol) in isopropanol (83 mL) was stirred overnight at room temperature. A precipitate formed. Water (100 mL) was added and the precipitate was collected. The precipitate was washed with water (50 mL) and vacuum dried to afford of 2-(2-methylbenzylidene)malononitrile (12.7 g) as a white solid (mp 105-106°). 1H-NMR (CDCl3) δ: 8.10 (s 1H); 8.08 (d, 1H); 7.50 (dd, 1H); 7.30-7.40 (m, 2H); 2,45 (s, 3H).

Workup

  1. customA precipitate formed
  2. customthe precipitate was collected
  3. washThe precipitate was washed with water (50 mL) and vacuum
  4. customdried

Sources & evidence

ORD record
ord-5d92d0c611404a04aae5d237bee3859c
Source dataset
uspto-grants-2004_03
Patent number
US06703420B1

Reaction notes

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