Hydrochloric Acid → 5-Bromo-2-methoxy-3-methylbenzoic acid

HRID 1771694Notes

Reaction equation

HRID 1771694 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].O.Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 2764346Methyl 5-bromo-2-methoxy-3-methylbenzoate

Product 1

HCID 9619195-Bromo-2-methoxy-3-methylbenzoic acidYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-bromo-2-methoxy-3-methyl-benzoate (2.6 g, 10.0 mmol, 1.0 eq) in THF (20 mL) was added an aqueous solution of NaOH (2M, 20 mL, 40 mmol, 4.0 eq). The mixture was stirred at room temperature for 5 h. Water was added and the aqueous layer was acidified to pH 9 by addition of 1M HCl. The THF was removed in vacuo and the aqueous layer was further acidified to pH 4-5 with 1M HCl. The solid that precipitated from the reaction was collected by filtration and dried to give the title compound as a white solid (1.8 g, 73%).

Workup

  1. customThe THF was removed in vacuo
  2. customThe solid that precipitated from the reaction
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-c47194d446964f7cb9ee6b669610bc9f
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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