Reaction #1885012

Reaction equation

Nitric acid

Ethyl 4-(4-ethanoyl-2-methoxylphenoxy)butanoate

→

ethyl 4-(4-ethanoyl-2-methoxy-5-nitrophenoxy)butanoate

Yield 45.3%

Solvents

water

Conditions

Workup

1. 1
   Otherdid not rise above 22° C
2. 2
   FiltrationThe product was collected via filtration
3. 3
   Otherrecrystallized from ethanol (250 mL)

Procedure

70% Nitric acid (60 mL) was cooled in an ice bath. Ethyl 4-(4-ethanoyl-2-methoxylphenoxy)butanoate (21 g, 0.075 mol) was added in portions over 20 minutes. The solution was stirred for 1.5 h while monitoring the temperature, which did not rise above 22° C. The solution was cautiously poured into water (800 mL), which was then cooled to 4° C. for several hours. The product was collected via filtration and recrystallized from ethanol (250 mL) to yield ethyl 4-(4-ethanoyl-2-methoxy-5-nitrophenoxy)butanoate (11.04 g, 45.3%) as a yellow flocculent powder. 1H NMR (δ, ppm): 1.31 (t, CO2CH2CH3), 2.21 (p, ArOCH2CH2CH2), 2.52 (s, ArCOCH3), 2.56 (t, ArOCH2CH2CH2), 3.98 (s, ArOCH3), 4.19 (m, ArOCH2 and CO2CH2), 6.76 (d, aromatic H ortho to ArOCH2), 7.65 (s, aromatic H ortho to ArOCH3).

Source