Acetonitrile → Acetonitrile, cyclohexylidene-

HRID 1060261Notes

Reaction equation

HRID 1060261 reaction equation
[OH-].[K+].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1(=O)CCCCC1.[C:16](#[N:18])[CH3:17]>O>[C:5]1(=[CH:17][C:16]#[N:18])[CH2:4][CH2:3][CH2:8][CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7967CyclohexanoneHCID 8058HexaneHCID 14797Potassium Hydroxide

Product 1

HCID 97105Acetonitrile, cyclohexylidene-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
55 °C

Procedure

A 10 l round-bottom flask is loaded with 285 g (4.57 mols) of 90% potassium hydroxide in flakes and 1775 ml of hexane. The mixture is heated to 55° C. and, keeping heating, a solution consisting of 450 g (4.59 mols) of cyclohexanone and 1351 ml of acetonitrile is quickly dropped therein (during the addition temperature falls to 52.6° C.). The mixture is refluxed for 7 hours, then cooled at room temperature. 2863 ml of water are added thereof to dissolve the solid. The organic phase is washed twice with water (1000 ml each). The phases are separated and the organic phase is evaporated to dryness under vacuum, to obtain 462 g of a residue which is distilled under 10 mmHg at 100-105° C.

Workup

  1. temperaturekeeping heating
  2. additionis quickly dropped
  3. customfalls to 52.6° C.
  4. temperatureThe mixture is refluxed for 7 hours
  5. temperaturecooled at room temperature
  6. dissolutionto dissolve the solid
  7. washThe organic phase is washed twice with water (1000 ml each)
  8. customThe phases are separated
  9. customthe organic phase is evaporated to dryness under vacuum

Sources & evidence

ORD record
ord-4103d33773a84c1f9fe0d0933d852729
Source dataset
uspto-grants-2003_02
Patent number
US06521788B2

Reaction notes

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