2,3,4-Trimethoxy-6-methylbenzaldehyde → 2,3,4-Trimethoxy-6-methylbenzoic acid

HRID 242437Notes

Reaction equation

HRID 242437 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[C:7]([CH3:15])[C:4]=1[CH:5]=[O:6].P([O-])(O)(O)=[O:17].[Na+].Cl([O-])=O.[Na+].C(=O)([O-])O.[Na+]>CS(C)=O>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[C:7]([CH3:15])[C:4]=1[C:5]([OH:17])=[O:6]

Participants

6

Reactant 4

HCID 896832,3,4-Trimethoxy-6-methylbenzaldehydeHCID 516892Sodium BicarbonateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 135314152,3,4-Trimethoxy-6-methylbenzoic acidYield 458.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

45.6 g (217 mmol) of 2,3,4-trimethoxy-6-methylbenzaldehyde was dissolved in 130 ml of dimethyl sulfoxide, and an aqueous solution (50 ml) of 5.2 g (44 mmol) of sodium dihydrogen phosphate was dropwise added over a period of 20 minutes. Then, an aqueous solution (180 ml) of 28 g (305 mmol) of sodium chlorite was dropwise added over a period of 3 hours, followed by stirring for 2 hours. A saturated sodium hydrogencarbonate aqueous solution was added until no bubbling occurred, followed by stirring for 1 hour. Then, the reaction solution was washed with 50 ml of ethyl acetate twice, and concentrated hydrochloric acid was added to make the aqueous layer acidic, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The obtained crystals were washed with hexane to obtain 45.6 g (yield: 93%) of 2,3,4-trimethoxy-6-methylbenzoic acid (melting point 95 to 97° C.).

Workup

  1. stirringby stirring for 1 hour
  2. washThen, the reaction solution was washed with 50 ml of ethyl acetate twice
  3. additionconcentrated hydrochloric acid was added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. washThe obtained crystals were washed with hexane

Sources & evidence

ORD record
ord-eb5e1b9832af4e1c898d0a2a428ee04d
Source dataset
uspto-grants-2014_02
Patent number
US08653113B2

Reaction notes

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