Hydrochloric Acid → (3-Methoxy-4-nitrobenzyl)phosphonic acid

HRID 511307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511307
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[CH2:6][P:7](=[O:14])([O:11]CC)[O:8]CC.Cl>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-:20])=[O:19])[CH2:6][P:7](=[O:8])([OH:11])[OH:14]

Komponenten

3

Edukt 2

HCID 313Hydrochloric AcidHCID 86654016Diethyl (3-methoxy-4-nitrobenzyl)phosphonate2×

Produkt 1

HCID 67256089(3-Methoxy-4-nitrobenzyl)phosphonic acid

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A suspension of diethyl (3-methoxy-4-nitrobenzyl)phosphonate (Compound 114E, 5.04 g, 16.6 mmol) in concentrated HCl (50.0 mL, 1630 mmol) was heated at 120° C. for a total of 16 h. After cooling to ambient temperature, the reaction mixture was concentrated in vacuo. After drying under vacuum for several hours, a solid had precipitated upon standing, giving the title material as a yellow solid, 4.1398 g (96%, 15.913 mmol). 1H NMR (DMSO-d6) δ ppm 7.81 (dd, J=8.3, 0.8 Hz, 1H), 7.23 (t, J=1.9 Hz, 1H), 6.99 (dt, J=8.3, 1.9 Hz, 1H), 5.75 (br s, 3H), 3.89 (s, 5H), 3.10 (d, J=22.0 Hz, 2H). MS (ES+): m/z 248.02 (100) [MH+]. HPLC: tR=1.68 min (ZQ3, polar—5 min).

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customAfter drying under vacuum for several hours
  4. customa solid had precipitated

Quellen und Nachweise

ORD-Eintrag
ord-75288a41daa542fd96ea5cb3700ec63c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096624B2

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