Hydrochloric Acid → 3-Bromo-6-hydroxy-2-methylbenzoic acid

HRID 365955Notes

Reaction equation

HRID 365955 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:14])=[C:6]([C:12]=1[CH3:13])[C:7]([O:9]CC)=[O:8].C(O)C.[OH-].[Na+].Cl>O>[OH:14][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[C:12]([CH3:13])[C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 23293235Ethyl 3-bromo-6-hydroxy-2-methylbenzoate

Product 1

HCID 110534513-Bromo-6-hydroxy-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1A (20.2 g, 0.078 mol), ethanol (150 ml) and an aqueous sodium hydroxide (12 g, 0.3 mol in 100 ml water) is heated under reflux with stirring for 16 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and acidified with concentrated hydrochloric acid. The precipitate is collected and washed with water yielding 18.45 g (100%) white crystals with a melting point of 163-165° C.

Workup

  1. temperatureunder reflux
  2. customThe precipitate is collected
  3. washwashed with water yielding 18.45 g (100%) white crystals with a melting point of 163-165° C.

Sources & evidence

ORD record
ord-1ca1a3967616418894d2d29c8c92c8a9
Source dataset
uspto-grants-2000_10
Patent number
US06127570

Reaction notes

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