Reaktion #1885011

Reaktionsgleichung

water

Acetovanillone

potassium carbonate

ethyl-4-bromobutyrate

→

ethyl 4-(4-ethanoyl-2-methoxyphenoxy)butanoate

Ausbeute 98.1%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for 24 h
2. 2
   SonstigeThe product was isolated by filtration

Vorschrift

Acetovanillone (16.6 g, 0.10 mol), potassium carbonate (30.0 g, 0.22 mol) and ethyl-4-bromobutyrate (17 mL, 0.12 mol) were combined in dimethylformamide (50 mL) and stirred under Argon for 17.5 h. The reaction was poured into water (800 mL) and stirred for 24 h. The product was isolated by filtration to yield ethyl 4-(4-ethanoyl-2-methoxyphenoxy)butanoate (27.5 g, 98%) as a white powder. 1H NMR (δ, ppm): 1.28 (t, CO2CH2CH3), 2.21 (p, ArOCH2CH2CH2), 2.56 (t, ArOCH2CH2CH2), 2.60 (s, ArCOCH3), 3.92 (s, ArOCH3), 4.13 (t, ArOCH2), 4.18 (q, CO2CH2), 6.92 (d, aromatic H ortho to ArOCH2), 7.54 (s, aromatic H ortho to ArOCH3), 7.58 (d, aromatic H ortho to ArCOCH3).

Quelle