Acetyl chloride → Cyclohexanone, 2-acetyl-3-butyl-

HRID 436535Notes

Reaction equation

HRID 436535 reaction equation
CC[CH2:3][CH2:4][CH2:5][CH3:6].C([Li])CCC.[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1.[C:19](Cl)(=[O:21])[CH3:20]>CCOCC.CN(C)P(=O)(N(C)C)N(C)C>[C:19]([CH:13]1[CH:14]([CH2:6][CH2:5][CH2:4][CH3:3])[CH2:15][CH2:16][CH2:17][C:12]1=[O:18])(=[O:21])[CH3:20]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 8058HexaneHCID 135942-Cyclohexen-1-oneHCID 178418339Butyllithium

Product 1

HCID 11310101Cyclohexanone, 2-acetyl-3-butyl-Yield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

In the same way as in Example 4, 15.3 ml (20 mmol) of a 1.31 M hexane solution of n-butyllithium was reacted with a solution of 960 mg (10 mmol) of 2-cyclohexenone in 5 ml of ether at -78° C for 30 minutes in the presence of 3.90 g (10 mmol) of tri-n-butylphosphine-copper (I) iodide complex. Then, a mixture consisting of 4 ml (56 mmol) of acetyl chloride, 5 ml of hexamethylphosphoric triamide and 10 ml of ether was rapidly added, and the mixture was stirred for 4 hours while gradually raising the temperature to room temperature. After the reaction, the reaction product was post-treated, extracted, washed, and dried in the same way as in Example 4 to afford 5.48 g of a crude product. The crude product was purified by distillation at reduced pressure to afford 1.81 g of 2-acetyl-3-n-butylcyclohexanone (boiling point 64° - 66° C/ 0.06 mmHg, 92%).

Workup

  1. additionwas rapidly added
  2. customAfter the reaction
  3. additionthe reaction product was post-treated
  4. extractionextracted
  5. washwashed
  6. customdried in the same way as in Example 4
  7. customto afford 5.48 g of a crude product
  8. distillationThe crude product was purified by distillation at reduced pressure

Sources & evidence

ORD record
ord-40ed7bb09aa941ce83baa29f13bbf511
Source dataset
uspto-grants-1977_02
Patent number
US04009196

Reaction notes

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