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

HRID 990070

Reaction equation

HRID 990070 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 afford 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-bc49a2cc0b734445bb4df2f685fd3820
Source dataset
uspto-grants-2002_10
Patent number
US06458805B2

Linked notes

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