Nitric Acid → Ethyl 4-(4-acetyl-2-methoxy-5-nitrophenoxy)butanoate

HRID 709325Notes

Reaction equation

[N+:1]([O-:4])(O)=[O:2].[C:5]([C:8]1[CH:22]=[CH:21][C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:10]([O:23][CH3:24])[CH:9]=1)(=[O:7])[CH3:6]>O>[C:5]([C:8]1[C:22]([N+:1]([O-:4])=[O:2])=[CH:21][C:11]([O:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:10]([O:23][CH3:24])[CH:9]=1)(=[O:7])[CH3:6]

Participants

Conditions

Temperature: 4 °C

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).

Workup

customdid not rise above 22° C
filtrationThe product was collected via filtration
customrecrystallized from ethanol (250 mL)

Sources & evidence

ORD record: ord-0339522a993844dd9271d2bad480cdb6
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09180196B2

Reaction notes

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