Nitric Acid → 1,4-Benzodioxan, 7-methyl-6-nitro-

HRID 395251Notes

Reaction equation

HRID 395251 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>C(O)(=O)C>[CH3:1][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 124003766-Methyl-2,3-dihydro-1,4-benzodioxine

Product 1

HCID 430871,4-Benzodioxan, 7-methyl-6-nitro-Yield 99.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 1 (20.0 g, 133.3 mmol) in acetic acid (135 mL) was added a solution of fuming HNO3 (10 mL) in acetic acid (50 mL) dropwise over 30 minutes. The mixture was stirred at ambient temperature for 10 minutes, then poured into a beaker containing ice to give a crystalline precipitate, which was collected by vacuum filtration and washed with water to afford the product (25.8 g, 99.2 %) as an off-white solid.

Workup

  1. additionpoured into a beaker
  2. additioncontaining ice
  3. customto give a crystalline precipitate, which
  4. filtrationwas collected by vacuum filtration
  5. washwashed with water

Sources & evidence

ORD record
ord-88369f025324472cb734ab481f9762b3
Source dataset
uspto-grants-2003_08
Patent number
US06605596B2

Reaction notes

Loading…