Sodium Chloride → Methyl 3-(3-methoxy-4-allyloxyphenyl)propionate

HRID 1448916

Reaktionsgleichung

Reaktionsgleichung von HRID 1448916
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][C:8]=1[OH:9].[OH-].[K+].[CH2:18](Br)[CH:19]=[CH2:20].[Na+].[Cl-]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH2:20][CH:19]=[CH2:18]

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 523498Methyl 3-(4-hydroxy-3-methoxyphenyl)propanoate

Produkt 1

HCID 20351150Methyl 3-(3-methoxy-4-allyloxyphenyl)propionateAusbeute 79,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

13.1 g methyl 3-(3-methoxy-4-hydroxyphenyl)propionate (62.4 mmol) is dissolved in 150 ml dry N,N-dimethylformamide (DMF). After addition of 4.0 g 88% KOH (62.7 mmol) to this solution, the whole is stirred for 30 minutes, after which 7.55 g allyl bromide (62.4 mmol) in 120 ml dry DMF is added dropwise over a 30-minute period. After stirring for 11/2 hours at room temperature, the reaction mixture is poured out into 1700 ml saturated NaCl solution. Extraction with ethyl acetate, evaporation to dryness and chromatography on 150 g silica gel with tolueneethyl acetate (95:5) as eluent gives 12.4 g methyl 3-(3-methoxy-4-allyloxyphenyl)propionate as an oil. Rf in toluene:ethyl-acetate (85.15)=0.5 on SiO2.

Aufarbeitung

  1. stirringAfter stirring for 11/2 hours at room temperature
  2. extractionExtraction
  3. customwith ethyl acetate, evaporation to dryness and chromatography on 150 g silica gel with tolueneethyl acetate (95:5) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-3db4a37ff0984b8f9adbf67a68cc2dad
Quelldatensatz
uspto-grants-1980_02
Patentnummer
US04188338

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