2-Nitropropane → 1,1-Dimethyl-2-hydroxy-2-(3,4-methylenedioxyphenyl)nitroethane

HRID 1680873Notes

Reaction equation

HRID 1680873 reaction equation
[Na].CO.[CH:4]1[C:9]([CH:10]=[O:11])=[CH:8][C:7]2[O:12][CH2:13][O:14][C:6]=2[CH:5]=1.[N+:15]([CH:18]([CH3:20])[CH3:19])([O-:17])=[O:16]>C(O)(=O)C>[CH2:13]1[O:14][C:6]2[CH:5]=[CH:4][C:9]([CH:10]([OH:11])[C:18]([CH3:20])([N+:15]([O-:17])=[O:16])[CH3:19])=[CH:8][C:7]=2[O:12]1

Participants

6

Reactant 4

HCID 3982-NitropropaneHCID 887MethanolHCID 8438PiperonalHCID 5360545Sodium

Product 1

HCID 234548521,1-Dimethyl-2-hydroxy-2-(3,4-methylenedioxyphenyl)nitroethaneYield 18.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7.7 g of sodium are added to 220 ml of anhydrous methanol, and 50 g of piperonal and 90 g of 2-nitropropane are added thereto. The mixture is stirred at room temperature for one hour, and then refluxed for 4 hours. After cooling, the reaction mixture is poured into ice-water containing 21 g of acetic acid, and then extracted with ether. The extract is washed with a saturated sodium chloride solution, a saturated sodium bisulfite solution and a saturated sodium chloride solution, successively. The washed extract is dried and then evaporated to remove solvent. 15 g of 1-(3,4-methylenedioxyphenyl)-2-methyl-2-nitropropanol are thereby obtained as a crude oil.

Workup

  1. additionare added
  2. temperaturerefluxed for 4 hours
  3. temperatureAfter cooling
  4. extractionextracted with ether
  5. washThe extract is washed with a saturated sodium chloride solution
  6. extractionThe washed extract
  7. customis dried
  8. customevaporated
  9. customto remove solvent

Sources & evidence

ORD record
ord-620d8dfb8e2f4ca3937f64c94380f825
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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