Thionyl Chloride → 5-(1-Chloro-2-methyl-2-nitropropyl)-2H-1,3-benzodioxole

HRID 1680874Notes

Reaction equation

HRID 1680874 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10](O)[C:11]([CH3:16])([N+:13]([O-:15])=[O:14])[CH3:12])=[CH:4][C:3]=2[O:2]1.S(Cl)([Cl:20])=O>C1C=CC=CC=1>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([Cl:20])[C:11]([CH3:16])([N+:13]([O-:15])=[O:14])[CH3:12])=[CH:4][C:3]=2[O:2]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 234548521,1-Dimethyl-2-hydroxy-2-(3,4-methylenedioxyphenyl)nitroethane

Product 1

HCID 234548395-(1-Chloro-2-methyl-2-nitropropyl)-2H-1,3-benzodioxoleYield 55.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 15 g of 1-(3,4-methylenedioxyphenyl)-2-methyl-2-nitropropanol (crude oil), 12 g of thionyl chloride and 80 ml of anhydrous benzene is refluxed for 3 hours. After the reaction, the reaction mixture is evaporated to remove solvent and thionyl chloride. The residue is purified by silica gel chromatography (Solvent: benzene). 9.0 g of 1-(3,4-methylenedioxyphenyl)-1-chloro-2-methyl-2-nitropropane are thereby obtained as an oil.

Workup

  1. temperatureis refluxed for 3 hours
  2. customAfter the reaction
  3. customthe reaction mixture is evaporated
  4. customto remove solvent and thionyl chloride
  5. customThe residue is purified by silica gel chromatography (Solvent: benzene)

Sources & evidence

ORD record
ord-e5ff0d8ae3ee40c786d3b97c961d1e14
Source dataset
uspto-grants-1981_06
Patent number
US04276304

Reaction notes

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