Hydrochloric Acid → 1-(5-Chloro-2,4-dimethoxyphenyl)ethan-1-one

HRID 2257123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2257123
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].[C:12](Cl)(=[O:14])[CH3:13].Cl>C(Cl)(Cl)(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[C:3]([O:10][CH3:11])=[CH:4][C:5]([O:8][CH3:9])=[C:6]([C:12](=[O:14])[CH3:13])[CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 1389051-Chloro-2,4-dimethoxybenzene

Produkt 1

HCID 24325931-(5-Chloro-2,4-dimethoxyphenyl)ethan-1-oneAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 2 g of 1-chloro-2,4-dimethoxybenzene and 0.9 g of acetyl chloride in 20 ml of CCl4 is cooled to 0° C., and a solution of 1.3 ml of TiCl4 in 7 ml of CCl4 is added dropwise. The reaction mixture is left stirring for 2 hours while the temperature is allowed to rise to r.t. It is poured into a mixture of concentrated HCl and ice, the resulting mixture is extracted with DCM, the organic phase is dried over magnesium sulphate and the solvents are evaporated off under vacuum. The residue is chromatographed on silica H, eluting with a DCM/heptane (70:30; v/v) mixture. 1.19 g of the expected product, m.p.=138° C., are obtained.

Aufarbeitung

  1. waitThe reaction mixture is left
  2. customto rise to r.t
  3. extractionthe resulting mixture is extracted with DCM
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. customthe solvents are evaporated off under vacuum
  6. customThe residue is chromatographed on silica H
  7. washeluting with a DCM/heptane (70:30; v/v) mixture

Quellen und Nachweise

ORD-Eintrag
ord-7a6ed299f81c4a6fbce5980aab570c5e
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05656648

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