2-Nitropropane → HCID 12439721, compound

HRID 1680866Notes

Reaction equation

HRID 1680866 reaction equation
[Na].CO.[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.[N+:14]([CH:17]([CH3:19])[CH3:18])([O-:16])=[O:15]>C(O)(=O)C>[CH3:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]([OH:11])[C:17]([CH3:19])([N+:14]([O-:16])=[O:15])[CH3:18])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 3982-NitropropaneHCID 887MethanolHCID 312444-MethoxybenzaldehydeHCID 5360545Sodium

Product 1

HCID 12439721HCID 12439721, compoundYield 13.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
13 °C

Procedure

11.5 g of sodium are added to 300 ml of anhydrous methanol, and 67 g of 4-methoxybenzaldehyde and 105 g of 2-nitropropane are added thereto at 13° C. for 25 minutes under stirring. The mixture is stirred at 23° C. for 70 hours. 32 g of acetic acid are added to the mixture under ice-cooling, and said mixture is evaporated under reduced pressure to remove solvent. About 200 ml of water are added to the residue, and the aqueous mixture is extracted with benzene. The extract is washed with a saturated sodium chloride solution, a saturated sodium bisulfite solution, water and a saturated sodium chloride solution, successively. The washed extract is dried and then evaporated to remove solvent. The residue (yellow oil, 65 g) is distilled at 75° C. under reduced pressure (1-2 mm Hg) to recover 47 g of the starting compound (i.e., 4-methoxybenzaldehyde). On the other hand, 14.5 g of 1-(4 -methoxyphenyl)-2-methyl-2-nitropropanol (crude product) are obtained as the residue.

Workup

  1. additionare added
  2. stirringThe mixture is stirred at 23° C. for 70 hours
  3. temperaturecooling
  4. customis evaporated under reduced pressure
  5. customto remove solvent
  6. additionAbout 200 ml of water are added to the residue
  7. extractionthe aqueous mixture is extracted with benzene
  8. washThe extract is washed with a saturated sodium chloride solution
  9. extractionThe washed extract
  10. customis dried
  11. customevaporated
  12. customto remove solvent
  13. distillationThe residue (yellow oil, 65 g) is distilled at 75° C. under reduced pressure (1-2 mm Hg)
  14. customto recover 47 g of the starting compound (i.e., 4-methoxybenzaldehyde)

Sources & evidence

ORD record
ord-c4b0f07f13714278b6e37389ae70483b
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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