2-Nitropropane → HCID 23454838, compound

HRID 1680870Notes

Reaction equation

HRID 1680870 reaction equation
[Na].[CH3:2][O:3][C:4]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].[N+:16]([CH:19]([CH3:21])[CH3:20])([O-:18])=[O:17]>CO.C(O)(=O)C>[CH3:2][O:3][C:4]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[CH:9]=[CH:8][C:5]=1[CH:6]([OH:7])[C:19]([CH3:21])([N+:16]([O-:18])=[O:17])[CH3:20]

Participants

6

Reactant 3

HCID 3982-NitropropaneHCID 750062,3,4-TrimethoxybenzaldehydeHCID 5360545Sodium

Product 1

HCID 23454838HCID 23454838, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Conditions

Temperature
15 °C

Procedure

6.4 g of sodium are added to 250 ml of anhydrous methanol, and 50 g of 2,3,4-trimethoxybenzaldehyde and 54.4 g of 2-nitropropane are added dropwise thereto at 15° C. for 40 minutes under stirring. The mixture is stirred at 25° C. for 24 hours, and 17 ml of acetic acid and 20 ml of methanol are added to said mixture under ice-cooling. The mixture is evaporated to remove solvent, and the residue is extracted with benzene. The extract is washed with water, an aqueous sodium bisulfite solution, water and a saturated sodium chloride solution, successively. The washed extract is dried and then evaporated to remove solvent. 63 g of 1-(2,3,4-trimethoxyphenyl)-2-methyl-2-nitropropanol are thereby obtained as a pale yellow oil.

Workup

  1. additionare added dropwise
  2. stirringThe mixture is stirred at 25° C. for 24 hours
  3. temperaturecooling
  4. customThe mixture is evaporated
  5. customto remove solvent
  6. extractionthe residue is extracted with benzene
  7. washThe extract is washed with water
  8. extractionThe washed extract
  9. customis dried
  10. customevaporated
  11. customto remove solvent

Sources & evidence

ORD record
ord-27fc991ab8664fa3ab159c6ec018cdda
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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