Hydrochloric Acid → 1-(4-Benzylthiophenyl)-2-(2-chloroethoxy)ethanol
Reaktionsgleichung
C([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[S:13])=[CH:10][CH:9]=1)C1C=CC=CC=1.[Cl:16][CH2:17][CH2:18][O:19][CH2:20][Mg]Cl.[Cl-].[NH4+].Cl.C([O:29][CH2:30][CH3:31])(=O)C>O1CCCC1>[CH2:12]([S:13][C:8]1[CH:15]=[CH:14][C:31]([CH:30]([OH:29])[CH2:20][O:19][CH2:18][CH2:17][Cl:16])=[CH:10][CH:9]=1)[C:11]1[CH:10]=[CH:9][CH:8]=[CH:15][CH:14]=1Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -10 °C
Versuchsvorschrift
1.19 g of 4-benzylthiobenzaldehyde was dissolved in 20 ml of tetrahydrofuran. The solution was cooled to -10° C. Thereto was dropwise added 10 ml of a tetrahydrofuran solution containing 2M of 2-chloroethoxymethylmagnesium chloride in 10 minutes. The resulting mixture was stirred for 1 hour with ice cooling. The reaction mixture was added to a mixture of 50 ml of ice water, 50 ml of ethyl acetate and 1 g of ammonium chloride. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by column chromatography [eluant: toluene/ethyl acetate=20/1] to obtain 1.34 g of 1-(4-benzylthiophenyl)-2-(2-chloroethoxy)ethanol.
Aufarbeitung
- customThe organic layer was separated
- washwashed with water
- dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
- customThe solvent was removed by distillation under reduced pressure
- customThe residue thus obtained
- customwas purified by column chromatography [eluant: toluene/ethyl acetate=20/1]
Quellen und Nachweise
- ORD-Eintrag
- ord-6c3c50818234425aa2ae8ed8e77986ce
- Quelldatensatz
- uspto-grants-1999_02
- Patentnummer
- US05872117
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