Acetic Acid → 2-Cyclohexylidenemalononitrile

HRID 1912949Notes

Reaction equation

HRID 1912949 reaction equation
C(O)(=O)C.[C:5](#[N:9])[CH2:6][C:7]#[N:8].[C:10]1(=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C1(C)C=CC=CC=1>[C:10]1(=[C:6]([C:5]#[N:9])[C:7]#[N:8])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7967CyclohexanoneHCID 8010Malononitrile

Product 1

HCID 203652-Cyclohexylidenemalononitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetic acid was added at room temperature to a stirring mixture of malononitrile (2.65 mL, 42.1 mmol), cyclohexanone (5.03 g, 51.3 mmol) and NH4OAc (6.49 g, 84 mmol) in toluene (200 mL). The resulting mixture was heated at reflux under a Dean-Stark trap for 2 hours (6 mL water collected), then cooled to room temperature. The mixture was concentrated under vacuum, and the residue was distilled under vacuum (air bath 110-130° C./˜10 mm) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.61-1.74 (m, 2H), 1.81 (ddt, J=6.5, 6.2, 5.8 Hz, 4H), 2.66 (dd, J=6.5, 6.2 Hz, 4H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under a Dean-Stark trap for 2 hours
  3. custom(6 mL water collected)
  4. concentrationThe mixture was concentrated under vacuum
  5. distillationthe residue was distilled under vacuum (air bath 110-130° C./˜10 mm)

Sources & evidence

ORD record
ord-02bee07bd47344a9ae52e227540f6fc2
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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