Hydrochloric Acid → 5-Bromo-2-methylbenzoic acid

HRID 1625770Notes

Reaction equation

HRID 1625770 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>CO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 316201Methyl 5-bromo-2-methylbenzoate

Product 1

HCID 3460045-Bromo-2-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 5-bromo-2-methylbenzoate (see Japanese Unexamined Patent Publication No. 9-263549) (16.12 g) was dissolved in methanol (100 ml), and thereto was added 10% aqueous sodium hydroxide solution (50 ml). The mixture was stirred at 50° C. for 40 minutes. Under ice-cooling, the mixture was adjusted to pH 1 by addition of 10% aqueous hydrochloric acid solution, and diluted with water. Precipitated powder was collected by filtration, and dried to give 5-bromo-2-methylbenzoic acid (14.1 g). ESI-Mass m/Z 213/215 (M−H).

Workup

  1. temperatureUnder ice-cooling
  2. customPrecipitated powder
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-a99d2c0a644640ccad829489b5d8430a
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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