Nitric Acid → HCID 10733790, compound

HRID 2289835Notes

Reaction equation

HRID 2289835 reaction equation
[C:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:6]([O:18][CH3:19])[CH:5]=1)(=[O:3])[CH3:2].[N+:20]([O-])([OH:22])=[O:21]>>[C:1]([C:4]1[C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:7]([O:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:6]([O:18][CH3:19])[CH:5]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 10849358Methyl 4-(4-acetyl-2-methoxyphenoxy)butanoate

Product 1

HCID 10733790HCID 10733790, compound

Procedure

Methyl 4-(4-acetyl-2-methoxyphenoxy)butyrate (10 g) was added to cold 70% nitric acid (140 cm3) and the resulting orange solution was stirred for 2 h and then poured into a beaker containg ice-water (1 dm3). The slurry warmed with stirring overnight to give a yellow solid which was collected and recrystallised from methanol to give methyl 4-(4-acetyl-2-methoxy-5-nitrophenoxy)butyrate as a pale yellow solid (8.5 g). 1H NMR (CDCl3) δ2.21 (2 H, m, J=6.6 Hz, CCH2C), 2.50 (3 H, s, MeCO), 2.57 (2 H, t, J=7.1 Hz, CH2CO), 3.7 (3 H, s, OMe), 3.99 (3 H, s, OMe), 4.16 (2 H, t, J=6.2 Hz, CH2O), 6.75 (1 H, s, aromatic) and 7.62 (1 H, s, aromatic).

Workup

  1. additionpoured into a beaker
  2. temperatureThe slurry warmed
  3. stirringwith stirring overnight
  4. customto give a yellow solid which
  5. customwas collected
  6. customrecrystallised from methanol

Sources & evidence

ORD record
ord-ce692f1de1c74014a8b74af2221310a5
Source dataset
uspto-grants-2000_07
Patent number
US06093798

Reaction notes

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