Dimethylformamide → Methyl 4-(3-chloropropoxy)benzoate

Reaktionsgleichung

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][Cl:11].CN(C)C=O.[OH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1>>[Cl:11][CH2:10][CH2:9][CH2:8][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:26][CH:27]=1

Komponenten

Edukt 4

HCID 6228Dimethylformamide

HCID 7456Methylparaben

HCID 80061-Bromo-3-chloropropane

HCID 11430Potassium Carbonate

Produkt 1

HCID 12389265Methyl 4-(3-chloropropoxy)benzoateAusbeute 93,7 %

Versuchsvorschrift

A suspension of potassium carbonate (48.4 g) in a mixture of methyl 4-hydroxybenzoate (10.65 g), 1-bromo-3-chloropropane (55.1 g) and N,N-dimethylformamide (100 mL) is stirred at room temperature for 15 h. Solids are separated by filtration and washed three times with ethanol (30 mL). The combined filtrates are concentrated under reduced pressure, and then dissolved in ethyl acetate (200 mL). The organic layer is washed twice with water (50 mL), dried over magnesium sulphate and concentrated under reduced pressure to give 15 g of methyl 4-(3-chloropropoxy)benzoate used without further purification.