Nitric Acid → 1-Acetoxy-2-[(3,4-methylenedioxy)-6-nitrophenyl]ethane

HRID 2270755Notes

Reaction equation

HRID 2270755 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH2:14][O:15][C:9]=2[CH:8]=1)(=[O:3])[CH3:2].[N+:16]([O-])([OH:18])=[O:17].O>C(O)(=O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][C:10]2[O:13][CH2:14][O:15][C:9]=2[CH:8]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 3030742-(1,3-Benzodioxol-5-yl)ethyl acetate

Product 1

HCID 234454281-Acetoxy-2-[(3,4-methylenedioxy)-6-nitrophenyl]ethaneYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 1-acetoxy-2-[(3,4-methylenedioxy)phenyl]ethane (1.7 g, 8.09 mmol) in acetic acid (10 ml) was added, dropwise, concentrated HNO3 (4.5 ml). This was stirred at room temperature for 30 min. The reaction mixture was poured into water (100 ml). The precipitated solid was filtered, washed with water and dried under high vacuum to get 1-acetoxy-2-[(3,4-methylenedioxy)-6-nitrophenyl]ethane (1.8 g, 88% yield).

Workup

  1. filtrationThe precipitated solid was filtered
  2. washwashed with water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-cd11da54ee2c4803a6dd340f7ba46110
Source dataset
uspto-grants-2001_12
Patent number
US06331637B1

Reaction notes

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