Acetone → 1-(4-Chlorophenyl)butane-1,3-dione

HRID 254450

Reaction equation

HRID 254450 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8]CC)=O)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:15][C:16]([CH3:18])=[O:17].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:8])[CH2:15][C:16](=[O:17])[CH3:18])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 81785Ethyl 4-chlorobenzoate

Product 1

HCID 2380831-(4-Chlorophenyl)butane-1,3-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture containing 45 g of ethyl 4-chlorobenzoate in 235 ml of anhydrous THF and 19.50 g of NaH (60% in mineral oil) in 235 ml of anhydrous TBF is placed under nitrogen. 36 ml of acetone and 750 ml of additional anhydrous THF are added dropwise at 0° C., and it is heated under reflux for 3 hours. The mixture is acidified to pH=5 by addition of 2N HCl then it is extracted with ether and washed with water and then with saturated NaHCO3 solution; it is dried over MgSO4 and concentrated. The raw product is dissolved in a minimum of toluene, the insoluble matter is filtered then it is purified by chromatography on silica, eluting with cyclohexane/AcOEt mixture (95/5; v/v). 47.9 g of the expected compound is obtained.

Workup

  1. temperatureit is heated
  2. temperatureunder reflux for 3 hours
  3. extractionit is extracted with ether
  4. washwashed with water
  5. dry with materialit is dried over MgSO4
  6. concentrationconcentrated
  7. dissolutionThe raw product is dissolved in a minimum of toluene
  8. filtrationthe insoluble matter is filtered
  9. customit is purified by chromatography on silica
  10. washeluting with cyclohexane/AcOEt mixture (95/5; v/v)

Sources & evidence

ORD record
ord-895a41e9b6884b8880e47028d75b1a0c
Source dataset
uspto-grants-2011_01
Patent number
US07875646B2

Linked notes

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