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

HRID 511307Notes

Reaction equation

HRID 511307 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
120 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-75288a41daa542fd96ea5cb3700ec63c
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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