Chloroacetone → 5,5-dimethyl-2-(2-oxopropyl)cyclohexane-1,3-dione

HRID 900480Notes

Reaction equation

HRID 900480 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:12])[CH2:9][C:8](=[O:10])[CH2:7][C:6](=[O:11])[CH2:5]1.Cl[CH2:14][C:15](=[O:17])[CH3:16].[NH4+].[Cl-]>CN(C=O)C>[CH3:3][C:4]1([CH3:12])[CH2:9][C:8](=[O:10])[CH:7]([CH2:14][C:15](=[O:17])[CH3:16])[C:6](=[O:11])[CH2:5]1

Participants

6

Reactant 4

HCID 6571ChloroacetoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 31358Dimedone

Product 1

HCID 14733595,5-dimethyl-2-(2-oxopropyl)cyclohexane-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

An oven dried flask was charged with sodium hydride (3.61 g, 142.7 mmol) to which 200 mL of anhydrous DMF was added. The flask was cooled in an ice bath before adding 5,5-dimethyl-1,3-cyclohexanedione (20.0 g, 142.7 mmol) and chloroacetone (11.36 mL, 142.7 mmol) in 100 mL DMF in a controlled manner. The reaction was allowed to warm to RT and stirred for 3 h. Saturated NH4Cl was added and the mixture was washed several times with EtOAc. The combined organic layer was dried over MgSO4, filtered, the solvent removed in vacuo (below 40° C.). LCMS m/z M+H=197.1.

Workup

  1. customAn oven dried flask
  2. additionwas added
  3. temperatureThe flask was cooled in an ice bath
  4. washthe mixture was washed several times with EtOAc
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo (below 40° C.)

Sources & evidence

ORD record
ord-94a74da35d9848e693c077e435e4d5d5
Source dataset
uspto-grants-2008_04
Patent number
US07358370B2

Reaction notes

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