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

HRID 2077471Notes

Reaction equation

HRID 2077471 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-e7c31535305a46f68ef03442609c422c
Source dataset
uspto-grants-2011_04
Patent number
US07928135B2

Reaction notes

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