Malononitrile → (1-Ethoxyethylidene)malononitrile

HRID 1782126Notes

Reaction equation

HRID 1782126 reaction equation
[C:1](OCC)(OCC)([O:3][CH2:4][CH3:5])[CH3:2].[C:12](#[N:16])[CH2:13][C:14]#[N:15]>C(O)(=O)C.C(O)C>[CH2:1]([O:3][C:4](=[C:13]([C:12]#[N:16])[C:14]#[N:15])[CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 8010MalononitrileHCID 66221Triethyl orthoacetate

Product 1

HCID 79450(1-Ethoxyethylidene)malononitrileYield 91.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

Triethyl orthoacetate (97 g, 0.6 mol), malononitrile (33 g, 0.5 mol) and glacial acetic acid (1.5 g) were placed in a 1 L flask equipped with a stirrer, thermometer and a Vigreux column (20×1 in.) on top of which a distillation condenser was placed. The reaction mixture was heated and ethyl alcohol began to distill when the temperature of the reaction mixture was about 85-90° C. After about 40 min., the temperature of the reaction mixture reached 140° C. Then the reaction was concentrated in a rotary evaporator to remove the low-boiling materials and the residue was crystallized from absolute alcohol to yield the pure product (62.2 g, 91%) as a light yellow solid mp 91.6° C.

Workup

  1. customequipped with a stirrer
  2. temperatureThe reaction mixture was heated
  3. distillationto distill when the temperature of the reaction mixture
  4. customwas about 85-90° C
  5. customreached 140° C
  6. concentrationThen the reaction was concentrated in a rotary evaporator
  7. customto remove the low-boiling materials
  8. customthe residue was crystallized from absolute alcohol

Sources & evidence

ORD record
ord-60798bafc8d2443e83492772e0af6030
Source dataset
uspto-grants-2009_03
Patent number
US07498333B2

Reaction notes

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