Sodium Carbonate → 3-Chloro-2-hydroxy-4-methoxybenzoic acid
Reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].P([O-])(O)(O)=[O:14].[Na+].Cl([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O.CS(C)=O>[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]([OH:14])=[O:6]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 15 °C
Procedure
To a solution of 3-chloro-2-hydroxy-4-methoxybenzaldehyde (16.6 g) and sodium dihydrogenphosphate (34.7 g) in a mixed solvent of DMSO (180 mL)-water (45.0 mL) was added an aqueous solution (35.0 mL) of sodium chlorite (27.2 g) under ice-cooling, and the mixture was stirred at 15° C. for 16 hr. The reaction mixture was poured into saturated aqueous sodium carbonate solution, the mixture was diluted with water, and filtered, and the filtrate was extracted with petroleum ether/ethyl acetate=5:1. The aqueous layer was acidified with conc. hydrochloric acid to adjusted pH=1, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (11.1 g).
Workup
- temperaturecooling
- filtrationfiltered
- extractionthe filtrate was extracted with petroleum ether/ethyl acetate=5:1
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with 1N hydrochloric acid
- dry with materialdried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-8cd53e5107f0418493cc58350d19959a
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315458B2
Reaction notes
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