Acetic Acid → Ethyl cyanocyclohexylideneacetate

HRID 1886897Notes

Reaction equation

HRID 1886897 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9].C(O)(=O)C.C([O-])(=O)C.[NH4+]>C1(C)C=CC=CC=1>[C:8]([C:10](=[C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])#[N:9]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 7967CyclohexanoneHCID 517165Ammonium Acetate

Product 1

HCID 81256Ethyl cyanocyclohexylideneacetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of cyclohexanone (1.50 ml, 14.47 mmol) in toluene (24.12 ml) was added ethyl cyanoacetate (1.556 ml, 14.62 mmol), acetic acid (0.166 ml, 2.89 mmol), and ammonium acetate (0.112 g, 1.447 mmol). The mixture was heated to a reflux at 150° C. in a Dean-Stark apparatus. After 5 h, the reaction was cooled and washed with water and saturated NaHCO3 solution. The organics were dried over Na2SO4, filtered, and concentrated.

Workup

  1. temperatureThe mixture was heated to
  2. temperaturethe reaction was cooled
  3. washwashed with water and saturated NaHCO3 solution
  4. dry with materialThe organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7397fbd2b4174c92958e3d305bcf2068
Source dataset
uspto-grants-2013_08
Patent number
US08501722B2

Reaction notes

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