Nitric Acid → Methyl 7-Nitro-1,4-benzodioxane-6-carboxylate

HRID 1595773Notes

Reaction equation

HRID 1595773 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]([C:9]1[CH:18]=[CH:17][C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[CH:10]=1)=[O:8]>CC(O)=O>[CH3:5][O:6][C:7]([C:9]1[C:18]([N+:1]([O-:4])=[O:2])=[CH:17][C:12]2[O:13][CH2:14][CH2:15][O:16][C:11]=2[CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 3802178Methyl 2,3-dihydro-1,4-benzodioxine-6-carboxylate

Product 1

HCID 10537941Methyl 7-Nitro-1,4-benzodioxane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Nitric Acid (18 mL) was added dropwise to a solution of 15.0 g (77.3 mmol) of 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester in 45 mL of HOAc. The solution was heated at 60° C. for 1.5 h. An additional 9 mL of HNO3 was then added and heating was continued for 1.5 h at 70° C. The reaction was poured into ice-H2O and the solid product was collected, washed well with H2O and dried. Recrystallization from heptane-toluene yielded 16.8 g of the title compound as yellow crystals: mass spectrum (electron impact, m/e): 239.

Workup

  1. temperatureheating
  2. customthe solid product was collected
  3. washwashed well with H2O
  4. customdried
  5. customRecrystallization from heptane-toluene

Sources & evidence

ORD record
ord-5fa3994982fb4aa182f96fb543f3e3c1
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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