Acetyl chloride → HCID 21568767, compound

HRID 1579555Notes

Reaction equation

HRID 1579555 reaction equation
N1CCCC1.[CH2:6]([CH:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)[CH3:7].C(NCC)C.[C:20](Cl)(=[O:22])[CH3:21]>O.C1C=CC=CC=1>[C:20]([CH:11]1[CH2:12][CH2:13][CH:8]([CH2:6][CH3:7])[CH2:9][C:10]1=[O:14])(=[O:22])[CH3:21]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8021DiethylamineHCID 31268PyrrolidineHCID 2283003-Ethylcyclohexanone

Product 1

HCID 21568767HCID 21568767, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Pyrrolidine (71.0 g.) is added to a solution of 12.6 g. of 3-ethylcyclohexanone in 12.6 ml. of benzene and the mixture is refluxed for eight hours with azeotropic removal of water. The mixture is cooled (ice bath) and 10.1 g. of diethylamine followed by 10.0 g. of acetyl chloride are added dropwise. The resulting mixture is refluxed for two hours then cooled and quenched by addition of 15.0 ml. of concentrated hydrochloric acid. The reaction mixture is refluxed an additional 15 minutes, cooled and diluted with water. The mixture is extracted with ether and the ethereal phase is washed with water, dried (MgSO4) and concentrated in vacuo to give a residue which, upon distillation in vacuo, gives 2-acetyl-5-ethylcyclohexanone.

Workup

  1. temperatureThe mixture is cooled (ice bath) and 10.1 g
  2. temperatureThe resulting mixture is refluxed for two hours
  3. temperaturethen cooled
  4. customquenched by addition of 15.0 ml
  5. temperatureThe reaction mixture is refluxed an additional 15 minutes
  6. temperaturecooled
  7. additiondiluted with water
  8. extractionThe mixture is extracted with ether
  9. washthe ethereal phase is washed with water
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo
  12. customto give a residue which
  13. distillationupon distillation in vacuo

Sources & evidence

ORD record
ord-8db0bdc15a0c49eea1e02e0ce0e909a1
Source dataset
uspto-grants-1976_01
Patent number
US03931232

Reaction notes

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