Water → Methyl 2,6-dichloro-4-hydroxybenzoate
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][C:7](N)=[CH:6][C:5]=1[Cl:12].N([O-])=[O:15].[Na+].O>Cl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([OH:15])=[CH:6][C:5]=1[Cl:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
4-Amino-2,6-dichlorobenzoic acid methyl ester (0.5 g) was suspended in 20% HCl (25 mL) and stirred for 30 min then cooled to 0-5° C. After slow addition of NaNO2 (188 mg), the mixture was stirred for 30 min at that temperature and added to boiling water (50 mL) . The mixture was then refluxed for 2 h, allowed to cool to room temperature and extracted with AcOEt, dried (MgSO4), filtered and evaporated. The residue was purified by preparative TLC (silica gel; eluent: CH2Cl2) to give 2,6-dichloro-4-hydroxybenzoic acid methyl ester (275 mg).
Workup
- stirringthe mixture was stirred for 30 min at that temperature
- additionadded
- temperatureThe mixture was then refluxed for 2 h
- temperatureto cool to room temperature
- extractionextracted with AcOEt
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
- customThe residue was purified by preparative TLC (silica gel; eluent: CH2Cl2)
Sources & evidence
- ORD record
- ord-bdcb123fafc840888d9620fda2c00d49
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06521666B1
Reaction notes
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