Methanol → 2-Methoxy-3-nitrobenzoic acid

HRID 629189Notes

Reaction equation

HRID 629189 reaction equation
[OH:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[OH-].[Na+].[CH3:17]O>>[CH3:17][O:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 596904Methyl 2-hydroxy-3-nitrobenzoate

Product 1

HCID 120151952-Methoxy-3-nitrobenzoic acidYield 93%

Procedure

Methyl 2-hydroxy-3-nitrobenzoate (2.85 g, 13.50 mmol) was dissolved in hot methanol (10 mL) at 75° C. to make clear solution and 1N aq. sodium hydroxide (28.3 mL, 28.3 mmol) was added dropwise. The mixture was heated under reflux for 15 minutes and then cooled to room temperature, concentrated to remove the methanol and then cooled in an ice bath. The solution was acidified via the dropwise addition of 1M (aq.) HCl until the pH was ˜1, resulting in the product precipitating out of solution. The solid was collected by filtration, rinsed with water, and dried on the filter to afford the product 2-methoxy-3-nitrobenzoic acid (2.48 g, 12.58 mmol, 93% yield) as a white solid. HPLC (Method N) RT=1.57 minutes.

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 15 minutes
  4. concentrationconcentrated
  5. customto remove the methanol
  6. temperaturecooled in an ice bath
  7. additionThe solution was acidified via the dropwise addition of 1M (aq.) HCl until the pH was ˜1
  8. customresulting in the product
  9. customprecipitating out of solution
  10. filtrationThe solid was collected by filtration
  11. washrinsed with water
  12. customdried on the
  13. filtrationfilter

Sources & evidence

ORD record
ord-94494e4f13ab468c8cabc17b68f6d17b
Source dataset
uspto-grants-2016_04
Patent number
US09315494B2

Reaction notes

Loading…