2-Nitropropane → Methyl 3-formyl-4-methylsulfonyl-2-methylbenzoate

HRID 1857311Notes

Reaction equation

HRID 1857311 reaction equation
CO.C[O-].[Na+].[N+](C(C)C)([O-])=[O:7].Br[CH2:13][C:14]1[C:15]([CH3:28])=[C:16]([CH:21]=[CH:22][C:23]=1[S:24]([CH3:27])(=[O:26])=[O:25])[C:17]([O:19][CH3:20])=[O:18]>Cl>[CH:13]([C:14]1[C:15]([CH3:28])=[C:16]([CH:21]=[CH:22][C:23]=1[S:24]([CH3:27])(=[O:26])=[O:25])[C:17]([O:19][CH3:20])=[O:18])=[O:7]

Participants

6

Reactant 4

HCID 3982-NitropropaneHCID 887Methanol2×HCID 10942334Sodium MethoxideHCID 22129433Methyl 3-bromomethyl-4-methanesulfonyl-2-methylbenzoate

Product 1

HCID 22129434Methyl 3-formyl-4-methylsulfonyl-2-methylbenzoateYield 88.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Into 20 ml of methanol was added 2.60 g of a methanol solution of 28% sodium methylate, and 1.30 g of 2-nitropropane was added dropwise at room temperature, followed by adding 4.40 g of methyl 3-bromomethyl-4-methylsulfonyl-2-methylbenzoate. The resulting solution was heated at reflux for an hour. After the reaction solution was cooled down, 50 ml of IN hydrochloric acid was added to the solution to extract with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure to give 3.10 g of the title compound as crystals. m.p. 108~110° C.

Workup

  1. additionwas added dropwise at room temperature
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux for an hour
  4. temperatureAfter the reaction solution was cooled down
  5. extractionto extract with ethyl acetate
  6. washThe organic layer was washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-9ed0adac67df40329fec6932434c3fa6
Source dataset
uspto-grants-2000_11
Patent number
US06147031

Reaction notes

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