Hydrochloric Acid → 1-(2,4-Dichlorophenyl)-2-(4-methoxyphenyl)ethanone

HRID 733286

Reaktionsgleichung

Reaktionsgleichung von HRID 733286
[Na].C[Si](C)(C)N[Si](C)(C)C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=O)=[CH:15][CH:14]=1.[Cl:23][C:24]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:25]=1C(OC)=O.Cl>C1COCC1>[Cl:23][C:24]1[CH:33]=[C:32]([Cl:34])[CH:31]=[CH:30][C:25]=1[C:20](=[O:22])[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][CH3:11])=[CH:18][CH:17]=1

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 76904-Methoxyphenylacetic AcidHCID 13838HexamethyldisilazaneHCID 37055Methyl 2,4-dichlorobenzoateHCID 5360545Sodium

Produkt 1

HCID 610554751-(2,4-Dichlorophenyl)-2-(4-methoxyphenyl)ethanoneAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

413 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to −65° C. under a nitrogen atmosphere, 300 ml of THF are added, a solution of 55 g of 4-methoxyphenylacetic acid in 70 ml of THF is then added dropwise and the mixture is left stirring for 3 hours at a temperature of less than −45° C. 64.5 g of methyl 2,4-dichlorobenzoate are subsequently added dropwise and the mixture is left stirring while allowing the temperature to rise to 0° C. The reaction mixture is poured onto an ice/1 liter of 2N HCl mixture and extracted with ether, the organic phase is washed with a saturated NaHCO3 solution and dried over Na2SO4, and the solvent is evaporated under vacuum. The residue is chromatographed on silica gel, elution being carried out with heptane and then with the heptane/AcOEt mixture up to (90/10; v/v). 29 g of the expected compound are obtained.

Aufarbeitung

  1. waitthe mixture is left
  2. waitthe mixture is left
  3. stirringstirring
  4. customto rise to 0° C
  5. extractionextracted with ether
  6. washthe organic phase is washed with a saturated NaHCO3 solution
  7. dry with materialdried over Na2SO4
  8. customthe solvent is evaporated under vacuum
  9. customThe residue is chromatographed on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-f304e214d6de4e7f830d0f20fc635329
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07589120B2

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