Nitric Acid → 4-Methoxy-6-nitro-1,3-benzodioxole

HRID 1179225

Reaction equation

HRID 1179225 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[N+:12]([O-])([OH:14])=[O:13]>C(OC(=O)C)(=O)C>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][O:8][C:7]=2[CH:6]=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5924784-Methoxybenzo[d][1,3]dioxole

Product 1

HCID 28250194-Methoxy-6-nitro-1,3-benzodioxoleYield 46%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

4-Methoxy-benzo[1,3]dioxole (2.03 g, 13.34 mmole) was dissolved in acetic anhydride (20 mL) and cooled in an ice bath while stirring. Nitric acid (1.5 mL) was added dropwise with an addition funnel over 30 minutes. The ice bath was removed and the mixture was stirred overnight allowing the reaction to heat up to room temperature. The mixture was poured into ice water and the product crashed out and was filtered and washed with water. The precipitate was dried under vacuum in a dessicator yielding (1.21 g, 46% yield) of 4-methoxy-6-nitro-benzo[1,3]dioxole. NMR-DMSO-d6: 7.63 (s, 1H), 7.52 (s, 1H), 6.25 (s, 2H), 3.95 (s, 3H)

Workup

  1. temperaturecooled in an ice bath
  2. customThe ice bath was removed
  3. stirringthe mixture was stirred overnight
  4. customthe reaction
  5. filtrationwas filtered
  6. washwashed with water
  7. customThe precipitate was dried under vacuum in a dessicator

Sources & evidence

ORD record
ord-f50ec239323c420fa35fc0d71c2f819d
Source dataset
uspto-grants-2007_10
Patent number
US07279469B2

Linked notes

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