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

HRID 52857

Reaktionsgleichung

Reaktionsgleichung von HRID 52857
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 241BenzeneLösungsmittel3×HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-43d94b084fa544dd890dfe8561624ccc
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616803

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