Nitric Acid → 6-Nitro-1,3-benzodioxole-5-carboxylic acid

HRID 1729202Notes

Reaction equation

HRID 1729202 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[N+:13]([O-])([OH:15])=[O:14]>O>[CH2:6]1[O:5][C:4]2[C:8](=[CH:9][C:10]([N+:13]([O-:15])=[O:14])=[C:2]([CH:3]=2)[C:1]([OH:12])=[O:11])[O:7]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 71961,3-Benzodioxole-5-carboxylic acid

Product 1

HCID 2464356-Nitro-1,3-benzodioxole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

30 g (0.18 mole) of piperonylic acid are added with care to 200 ml of nitric acid (d=1.42). After a first addition of 5 g, the reaction is started by heating and by vigorously stirring the reaction mixture at 50° C. The addition of the remaining 25 g is carried out in small fractions. At the end of the addition, the reaction mixture is left stirring for 2 hours. Then 200 ml of water are added, the insoluble reaction product is spun, washed with 100 ml of water and then dissolved in a saturated aqueous solution of sodium bicarbonate. The insoluble compounds are removed. The filtrate is acidified at 0° C. and the precipitate is collected and then spun, washed with water and dried.

Workup

  1. additionAfter a first addition of 5 g
  2. temperatureby heating
  3. additionThe addition of the remaining 25 g
  4. additionAt the end of the addition
  5. waitthe reaction mixture is left
  6. stirringstirring for 2 hours
  7. washwashed with 100 ml of water
  8. dissolutiondissolved in a saturated aqueous solution of sodium bicarbonate
  9. customThe insoluble compounds are removed
  10. customis acidified at 0° C.
  11. customthe precipitate is collected
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-7d7a4b8b90b34e038e28c843fe48b9c7
Source dataset
uspto-grants-1994_07
Patent number
US05332735

Reaction notes

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