Hydroxyamine hydrochloride → Methyl 3-hydroxyiminomethyl-4-methylsulfonyl-2-methylbenzoate

HRID 1857312Notes

Reaction equation

HRID 1857312 reaction equation
[CH:1]([C:3]1[C:4]([CH3:17])=[C:5]([CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7])=O.Cl.[NH2:19][OH:20]>C(O)C>[OH:20][N:19]=[CH:1][C:3]1[C:4]([CH3:17])=[C:5]([CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 22129434Methyl 3-formyl-4-methylsulfonyl-2-methylbenzoate

Product 1

HCID 86756010Methyl 3-hydroxyiminomethyl-4-methylsulfonyl-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.55 g of methyl 3-formyl-4-methylsulfonyl-2-methylbenzoate was dissolved in 100 ml of ethanol, and 4.70 g of hydroxylamine hydrochloride was added. The resulting solution was reacted for 1.5 hours at room temperature and further heated at reflux for an hour. The reaction solution was cooled down. Ethanol was then distilled out under reduced pressure. The obtained residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with water and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure to give 12.31 g of a crude product as viscous oil. The crude product was purified by column chromatography on silica gel with n-hexane/ethyl acetate=2/1 to give the title compound as white crystals. m.p. 123~129° C.

Workup

  1. customThe resulting solution was reacted for 1.5 hours at room temperature
  2. temperaturefurther heated
  3. temperatureat reflux for an hour
  4. temperatureThe reaction solution was cooled down
  5. distillationEthanol was then distilled out under reduced pressure
  6. dissolutionThe obtained residue was dissolved in ethyl acetate
  7. washThe ethyl acetate solution was washed with water
  8. dry with materiala saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled out under reduced pressure
  10. customto give 12.31 g of a crude product as viscous oil
  11. customThe crude product was purified by column chromatography on silica gel with n-hexane/ethyl acetate=2/1

Sources & evidence

ORD record
ord-5bc687f92a094bc59fa16d0cbd707e30
Source dataset
uspto-grants-2000_11
Patent number
US06147031

Reaction notes

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