Benzene → 2-Acetyl-4-methoxycyclohexanone

HRID 980913Notes

Reaction equation

HRID 980913 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]1[CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]1.C1C=CC=CC=1.Cl.[C:19](OCC)(=[O:21])[CH3:20]>O.CO>[C:19]([CH:9]1[CH2:10][CH:5]([O:4][CH3:3])[CH2:6][CH2:7][C:8]1=[O:11])(=[O:21])[CH3:20]

Participants

8

Reactant 5

HCID 241BenzeneHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydride2×HCID 5350284-Methoxycyclohexanone

Product 1

HCID 136327242-Acetyl-4-methoxycyclohexanoneYield 49.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 60% sodium hydride (1.12 g) in 2.5 g of ethyl acetate, a solution consisting of 1.78 g of 4-methoxycyclohexanone and 0.5 ml of benzene was dropwise added. The reaction was allowed to proceed at 40° C. for 3 hours and then at room temperature for 3 hours. A small amount of methanol was added to decompose the sodium hydride. The reaction mixture was then poured into water, neutralized with hydrochloric acid, and extracted with ether. Thus, 1.16 g of 2-acetyl-4-methoxycyclohexanone was obtained.

Workup

  1. additionwas dropwise added
  2. waitat room temperature for 3 hours
  3. extractionextracted with ether

Sources & evidence

ORD record
ord-a56093ae54274036b1ec77c14444353f
Source dataset
uspto-grants-1987_01
Patent number
US04639521

Reaction notes

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