Nitric Acid → 5-Nitro-4,7-dimethyl-1,3-benzodioxole

HRID 1376554Notes

Reaction equation

HRID 1376554 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[C:14]2[O:13][CH2:12][O:11][C:10]=2[C:9]([CH3:15])=[CH:8][CH:7]=1>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(OC(=O)C)(=O)C>[N+:1]([C:8]1[CH:7]=[C:6]([CH3:5])[C:14]2[O:13][CH2:12][O:11][C:10]=2[C:9]=1[CH3:15])([O-:4])=[O:2]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 125809854,7-Dimethyl-1,3-benzodioxole

Product 1

HCID 218404755-Nitro-4,7-dimethyl-1,3-benzodioxole

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

A solution of 0.92 mL of concentrated nitric acid in 17 mL of acetic arthydride is added dropwise to a stirred solution of 2.20 g of 4,7-dimethyl-1,3-benzodioxole in 60 mL of acetic anhydride at -5° C. After 30 minutes, the mixture is poured over 100 g of crushed ice and allowed to stir for 30 minutes as a white precipitate falls out of solution. The solid is filtered, taken up in ether, dried over magnesium sulfate and concentrated under reduced pressure to afford 2.1 g of 5-nitro-4,7-dimethyl-1,3-benzodioxole.

Workup

  1. filtrationThe solid is filtered
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4649a188f544ee48bbdcd0d15e73bf3
Source dataset
uspto-grants-1997_09
Patent number
US05663189

Reaction notes

Loading…