Hydrochloric Acid → Methyl 3-formyl-4-methylsulfonyl-2-methylbenzoate

HRID 1857310Notes

Reaction equation

HRID 1857310 reaction equation
Br[CH2:2][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].C[N+]1([O-])CC[O:22]CC1.Cl>C(#N)C>[CH:2]([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:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 82029Methyl morpholine oxideHCID 22129433Methyl 3-bromomethyl-4-methanesulfonyl-2-methylbenzoate

Product 1

HCID 22129434Methyl 3-formyl-4-methylsulfonyl-2-methylbenzoateYield 76.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

18.90 g of methyl 3-bromomethyl-4-methylsulfonyl-2-methylbenzoate was dissolved in 180 ml of acetonitrile, and 20.67 g of N-methylmorpholine oxide was added over 10 minutes at room temperature. The resulting solution was stirred at room temperature for an hour, poured into ice water, acidified with concentrated hydrochloric acid, and extracted with benzene. The organic layer was washed with water, then with a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure to give 11.59 g of the title compound as white crystals. The crude product was washed with ethanol to give white crystals of the title compound. m.p. 108~110° C.

Workup

  1. extractionextracted with benzene
  2. washThe organic layer was washed with water
  3. dry with materialwith a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-d088603115574f83a1ac61a468668d22
Source dataset
uspto-grants-2000_11
Patent number
US06147031

Reaction notes

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