Nitric Acid → 1-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanone

HRID 2358999Notes

Reaction equation

HRID 2358999 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:20]([O-])([OH:22])=[O:21].O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:18][CH3:19])=[CH:11][C:12]([C:15](=[O:17])[CH3:16])=[C:13]([N+:20]([O-:22])=[O:21])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 992151-(4-Benzyloxy-3-methoxy-phenyl)-ethanone

Product 1

HCID 534867601-(4-(Benzyloxy)-5-methoxy-2-nitrophenyl)ethanoneYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

1-(4-Benzyloxy-3-methoxy-phenyl)-ethanone (24.61 g, 96 mmol) was dissolved in acetic acid (100 ml) and the mixture was cooled to 10° C. Nitric acid fuming (Fluka ID 84392, 100%, 10 ml, 240 mmol) was added dropwise to the cooled solution over 2 hours. The reaction mixture was allowed to come to room temperature and stirred for 16 hours. The reaction mixture was poured into water (400 ml). The precipitate was filtered, washed with water, then taken up in sodium hydrogencarbonate saturated aqueous solution (300 ml) and stirred for 2 hours. The precipitate was filtered, washed with water and dried. The raw product was recrystallized from ethyl alcohol (1000 ml) to give 18.25 g of product [B]. Yield 65%.

Workup

  1. customto come to room temperature
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. stirringstirred for 2 hours
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried
  8. customThe raw product was recrystallized from ethyl alcohol (1000 ml)

Sources & evidence

ORD record
ord-4e45f609fad54ade9c29b419d4bba9c1
Source dataset
uspto-grants-2014_04
Patent number
US08685971B2

Reaction notes

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