Nitric Acid → 5-nitro-2-phenyl-1,3-benzodioxole

HRID 262959Notes

Reaction equation

HRID 262959 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH2:2]1.[N+:10]([O-:13])(O)=[O:11]>>[N+:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH:2]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[O:3][C:4]=2[CH:9]=1)([O-:13])=[O:11]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 92291,3-Benzodioxole

Product 1

HCID 2795175-nitro-2-phenyl-1,3-benzodioxole

Procedure

A solution of 39.6 g (0.2 mol) of the benzodioxolan obtained as just described in 150 ml of acetic acid ester was added dropwise at 25° to 35° C. to 150 ml of a 33% nitric acid. The solution was poured into ice water after 2 hours and then extracted several times with acetic ester. The combined acetic ester phases were then washed several times with a solution of potassium bicarbonate and then with water, followed by drying and evaporation by concentration. Crystallization from ethanol furnished 37 g of a product of the melting point between 84° and 85° C.

Workup

  1. extractionextracted several times with acetic ester
  2. washThe combined acetic ester phases were then washed several times with a solution of potassium bicarbonate
  3. customby drying
  4. customevaporation
  5. concentrationby concentration
  6. customCrystallization from ethanol

Sources & evidence

ORD record
ord-ef6bdfb48bb0487f9235881473eab142
Source dataset
uspto-grants-1979_05
Patent number
US04155915

Reaction notes

Loading…