Citric Acid → 4-(3,4-Dichlorophenyl)-3-(4-dimethoxymethylphenyl)-2-butanone

HRID 1956064Notes

Reaction equation

HRID 1956064 reaction equation
[H-].[Na+].[CH3:3][O:4][CH:5]([O:16][CH3:17])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1.[Cl:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][C:26]=1[Cl:27])[CH2:22]Cl.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O.C1C=CC=CC=1.C(OCC)C>[Cl:18][C:19]1[CH:20]=[C:21]([CH2:22][CH:12]([C:9]2[CH:10]=[CH:11][C:6]([CH:5]([O:4][CH3:3])[O:16][CH3:17])=[CH:7][CH:8]=2)[C:13](=[O:15])[CH3:14])[CH:24]=[CH:25][C:26]=1[Cl:27]

Participants

8

Reactant 4

HCID 311Citric AcidHCID 76093,4-Dichlorobenzyl chlorideHCID 24758Sodium hydrideHCID 190736824-Dimethoxymethylphenylacetone

Product 1

HCID 190737314-(3,4-Dichlorophenyl)-3-(4-dimethoxymethylphenyl)-2-butanoneYield 46%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent3×HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent3×

Procedure

0.15 g of 60% oily sodium hydride was dissolved in a liquid mixture of 1.5 ml of dimethylformamide and 1.5 ml of benzene, and a dimethylformamide 2 ml/benzene 2 ml solution of 0.72 g of 4-dimethoxymethylphenylacetone was dropwise added thereto with stirring under cooling with ice. The mixture was stirred at the same temperature for 15 minutes. To this solution, a dimethylformamide 2 ml/benzene 2 ml solution of 0.65 ml of 3,4-dichlorobenzyl chloride was dropwise added with stirring under cooling with ice. The mixture was stirred at the same temperature for 40 minutes. Then, a 3% citric acid aqueous solution and ethyl ether were added for liquid separation. The organic layer was collected by separation, then washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was subjected to medium pressure liquid chromatography (Lobar column™, size B, Lichroprep™ Si60F, manufactured by Merck Co.; hexane/ethyl acetate=10/1→6/1) to obtain 0.64 g (yield: 46%) of 4-(3,4-dichlorophenyl)-3-(4-dimethoxymethylphenyl)-2-butanone as colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe mixture was stirred at the same temperature for 15 minutes
  3. stirringwith stirring
  4. temperatureunder cooling with ice
  5. stirringThe mixture was stirred at the same temperature for 40 minutes
  6. customThe organic layer was collected by separation
  7. washwashed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e6d1970498b84a04a7e102a2eedda21e
Source dataset
uspto-grants-1998_07
Patent number
US05777150

Reaction notes

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