Water → 1-(3-Chloro-2-methoxymethoxyphenyl)-1-(2-methoxyphenyl)ethanol

HRID 466928

Reaktionsgleichung

Reaktionsgleichung von HRID 466928
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][O:10][CH3:11].[CH2:12]([Li])[CH2:13][CH2:14][CH3:15].[CH3:17][O:18][CH2:19][C:20]([C:22]1C=CC=C[CH:23]=1)=O.[OH2:28]>CCCCCC.O1CCCC1.CCOCC>[Cl:1][C:2]1[C:3]([O:8][CH2:9][O:10][CH3:11])=[C:4]([C:14]([C:13]2[CH:12]=[CH:23][CH:22]=[CH:20][C:19]=2[O:18][CH3:17])([OH:28])[CH3:15])[CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 776982-Methoxy-1-phenylethanoneHCID 5426241-Chloro-2-(methoxymethoxy)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 198126791-(3-Chloro-2-methoxymethoxyphenyl)-1-(2-methoxyphenyl)ethanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

1-Chloro-2-methoxymethoxybenzene (20.0 g) was combined with 72.5 ml of 1.6M n-butyl lithium in hexane at 0° C. with stirring and allowed to react for 4 hours. A solution of 16.0 ml of 2-methoxyacetophenone in 20 ml of tetrahydrofuran was then added with stirring. After a short reaction period, water and ether were added and the ether layer was dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain an oil. This was purified by liquid chromatography, eluting with a 95:5 mixture of hexane and ethyl acetate, to obtain 6.67 g of the title compound as an oil. The assigned structure was consistent with the proton NMR spectrum.

Aufarbeitung

  1. customto react for 4 hours
  2. stirringwith stirring
  3. additionwere added
  4. dry with materialthe ether layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customto obtain an oil
  8. customThis was purified by liquid chromatography
  9. washeluting with a 95:5 mixture of hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-705f1d690a2745dc9345fff0a2678cc0
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158597

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