Hydrogen Peroxide → 3-(3-Chloropropoxy)-4-methoxy-6-nitrobenzoic acid

HRID 1803020Notes

Reaction equation

HRID 1803020 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:11]([N+:16]([O-:18])=[O:17])=[CH:12][C:13]=1[O:14][CH3:15])[CH:9]=[O:10].[OH-:19].[Na+].OO>CO>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:11]([N+:16]([O-:18])=[O:17])=[CH:12][C:13]=1[O:14][CH3:15])[C:9]([OH:19])=[O:10]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium Hydroxide2×HCID 250518443-(3-Chloropropoxy)-4-methoxy-6-nitrobenzaldehyde

Product 1

HCID 230330043-(3-Chloropropoxy)-4-methoxy-6-nitrobenzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanol (4 lt), 3-(3-chloropropoxy)-4-methoxy-6-nitro benzaldehyde (560 gm) and 30% methanolic NaOH solution (5 ml) were heated to 45° C. To this reaction mass 35% of H2O2 solution (1200 ml) was added drop wise in 3-4 hours maintaining a pH of 10.5-11.5 with 30% methanolic NaOH solution. The reaction mass was quenched into ice water (10 kg) and the pH adjusted to 2.0-3.0 using hydrochloric acid. The solid obtained was filtered, washed with 50% aqueous methanol (500 ml) and dried at 45-50° C. to yield the title compound (510 gm, 86% yield).

Workup

  1. customThe reaction mass was quenched into ice water (10 kg)
  2. customThe solid obtained
  3. filtrationwas filtered
  4. washwashed with 50% aqueous methanol (500 ml)
  5. customdried at 45-50° C.

Sources & evidence

ORD record
ord-9e41eda3d26c4256933a81a477637ade
Source dataset
uspto-grants-2013_01
Patent number
US08350029B2

Reaction notes

Loading…