Pyridine → 5,5-Dimethyl-3-oxocyclohex-1-en-1-yl acetate

HRID 2084280Notes

Reaction equation

HRID 2084280 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1([CH3:14])[CH2:11][C:10](=[O:12])[CH2:9][C:8](=[O:13])[CH2:7]1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[C:1]([O:12][C:10]1[CH2:11][C:6]([CH3:14])([CH3:5])[CH2:7][C:8](=[O:13])[CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 31358Dimedone

Product 1

HCID 108992885,5-Dimethyl-3-oxocyclohex-1-en-1-yl acetateYield 96.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acetyl chloride (1.1 ml, 15.65 mmol) was added to a stirred solution of 5,5-dimethyl-cyclohexane-1,3-dione (2.1 g, 14.23 mmol) and pyridine (1.14 ml), in chloroform (50 ml). The mixture was stirred at room temperature for about 1.5 hours, then washed with water, 0.1N HCl, saturated aqueous sodium hydrogen carbonate and water. The organic phase was dried over sodium sulfate and evaporated to dryness to give 2.5 g (96%) of the title compound as a colourless oil, which was used as such without any further purification.

Workup

  1. washwashed with water, 0.1N HCl, saturated aqueous sodium hydrogen carbonate and water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-efaf1dabc53c4df7a35d7d91a9f4ec50
Source dataset
uspto-grants-2004_04
Patent number
US06716856B1

Reaction notes

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