Sodium Carbonate → 4-Cyano-2-hydroxy-3-methylbenzoic acid

HRID 629370Notes

Reaction equation

[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([CH3:11])[C:4]=1[OH:12])=[O:2].P([O-])(O)(O)=[O:14].[Na+].Cl([O-])=O.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CS(C)=O>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([C:1]([OH:14])=[O:2])=[C:4]([OH:12])[C:5]=1[CH3:11])#[N:8]

Participants

Conditions

Temperature: 17 °C

Procedure

To a solution of 4-formyl-3-hydroxy-2-methylbenzonitrile (3.90 g) in DMSO (21.0 mL) were added sodium dihydrogenphosphate (7.26 g) and an aqueous solution (16.0 mL) of sodium chlorite (5.46 g) under ice-cooling, and the mixture was stirred at 17° C. for 16 hr. The reaction mixture was poured into saturated aqueous sodium carbonate solution, and the mixture was extracted with tert-butyl methyl ether. The aqueous layer was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (4.00 g: containing DMSO).

Workup

extractionthe mixture was extracted with tert-butyl methyl ether
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-41e05640bb3e42e284e545f831b210ff
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315458B2

Reaction notes

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