Sodium Hydroxide → 5-Bromo-2-methoxy-4-methylbenzoic acid

HRID 730626Notes

Reaction equation

HRID 730626 reaction equation
[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CCO.O>[Br:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21043961Methyl 5-bromo-2-methoxy-4-methylbenzoate

Product 1

HCID 186873935-Bromo-2-methoxy-4-methylbenzoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Methyl 5-bromo-2-methoxy-4-methylbenzoate (11.64 g, 0.045 mol) was dissolved in a mixture of EtOH:H2O (1:1 ratio, 150 mL), NaOH (5.8 g, 0.145 mol) was added and reaction mixture was refluxed for 30 min. The EtOH solvent was removed from the mixture by distillation which leads to precipitation of the desired product as its sodium salt. The residue was diluted with H2O (75 mL) and the pH was adjusted to ˜2 with concentrated HCl. The precipitate was collected by filtration, washed with H2O (3×50 mL) and air dried to give pure 5-bromo-2-methoxy-4-methylbenzoic acid 12a (9 g, 82% yield) as a beige solid.

Workup

  1. additionwas added
  2. customreaction mixture
  3. temperaturewas refluxed for 30 min
  4. customThe EtOH solvent was removed from the mixture by distillation which
  5. customleads to precipitation of the desired product as its sodium salt
  6. additionThe residue was diluted with H2O (75 mL)
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with H2O (3×50 mL) and air
  9. customdried

Sources & evidence

ORD record
ord-91ede3a32f1c487d88b729e501ab50b8
Source dataset
uspto-grants-2009_09
Patent number
US07582766B2

Reaction notes

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