Diethyl Ether → 3-Butylcyclohexanone

HRID 436536

Reaction equation

HRID 436536 reaction equation
C([O:3][CH2:4][CH3:5])C.[CH2:6]([Li])[CH2:7][CH2:8][CH3:9].[C:11]1(=[O:17])[CH2:16][CH2:15][CH2:14][CH:13]=[CH:12]1.C(Cl)(=O)C>CCCCCC>[CH2:6]([CH:13]1[CH2:14][CH2:15][CH2:16][C:11](=[O:17])[CH2:12]1)[CH2:7][CH2:8][CH3:9].[C:4]([CH:12]1[CH:13]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:14][CH2:15][CH2:16][C:11]1=[O:17])(=[O:3])[CH3:5]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 135942-Cyclohexen-1-oneHCID 178418339Butyllithium

Product 2

HCID 5661933-ButylcyclohexanoneHCID 11310101Cyclohexanone, 2-acetyl-3-butyl-

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To 20 ml of anhydrous diethyl ether was added 1.9 g (10 mmol) of cuprous iodide, and at -78° C in an atmosphere of nitrogen, 12.8 ml (20 mmol) of a 15 % by weight hexane solution of n-butyllithium was added. The mixture was stirred for 30 minutes, and then, 960 mg (10 mmol) of 2-cyclohexenone was added. The mixture was further stirred for one hour. Then, 3.93 g (50 mmol) of acetyl chloride was added, and the mixture was stirred for 2 hours at 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 2.662 g of a crude product. The crude product was purified by column chromatography (silica gel) to afford 56 mg (0.4 mmol) of 3-n-butylcyclohexanone as a by-product in a yield of 4% and 1.103 g (5.6 mmol) of 2-acetyl-3-n-butylcyclohexanone as a main product in a yield of 56%.

Workup

  1. stirringThe mixture was further stirred for one hour
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. customAfter the reaction
  4. additionthe reaction product was post-treated
  5. extractionextracted
  6. washwashed
  7. customdried in the same way as in Example 4
  8. customto afford 2.662 g of a crude product
  9. customThe crude product was purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-8f8cebf8f8dd43fe8b942042a16aec72
Source dataset
uspto-grants-1977_02
Patent number
US04009196

Linked notes

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