Sodium Hydroxide → 4-(2-Methylpropoxy)-3-nitrobenzoic acid

HRID 851859Notes

Reaction equation

HRID 851859 reaction equation
[CH2:1]([O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])[CH:2]([CH3:4])[CH3:3].[OH-].[Na+]>CO.C1COCC1>[CH2:1]([O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[N+:16]([O-:18])=[O:17])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 23023853HCID 23023853, compound

Product 1

HCID 230238474-(2-Methylpropoxy)-3-nitrobenzoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-isobutyloxy-3-nitrobenzoate (2.50 g, 9.87 mmol) was dissolved in a mixture of methanol (10 mL) and 25 THF (10 mL). After addition of 2M aqueous sodium hydroxide (7.5 mL, 15.0 mmol), the solution was stirred for 18 hours at room temperature. The solvent was distilled off under reduced pressure, and were added to the residue water (20 mL) and 3M aqueous hydrochloric acid to adjust 30 the solution to pH 1. The precipitated crystalline product was collected by filtration. The crystalline product was washed with water (20 mL×2) and dried at 50° C. for 4 hours under reduced pressure, to give 2.31 g (yield 98%) of the desired compound in the form of a white crystalline product.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionwere added to the residue water (20 mL) and 3M aqueous hydrochloric acid
  3. filtrationThe precipitated crystalline product was collected by filtration
  4. washThe crystalline product was washed with water (20 mL×2)
  5. customdried at 50° C. for 4 hours under reduced pressure

Sources & evidence

ORD record
ord-72a186cea1e94986b168aa974f6763a2
Source dataset
uspto-grants-2007_08
Patent number
US07253154B2

Reaction notes

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