Nitric Acid → 4-(Benzyloxy)-5-methoxy-2-nitrobenzonitrile

HRID 749151Notes

Reaction equation

HRID 749151 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=1[O:21][CH3:22])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)(=O)C>[CH2:5]([O:12][C:13]1[CH:20]=[C:19]([N+:1]([O-:4])=[O:2])[C:16]([C:17]#[N:18])=[CH:15][C:14]=1[O:21][CH3:22])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 7937714-Benzyloxy-3-methoxy-benzonitrile

Product 1

HCID 116736184-(Benzyloxy)-5-methoxy-2-nitrobenzonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
23 °C

Procedure

Acetic acid (17 ml) was added slowly to nitric acid (40 ml, 440 mmol) at 5° C. Powdered 4-benzyloxy-3-methoxybenzonitrile (10 g, 42 mmol) was added and the mixture warmed to 23° C. over 10 minutes. An exotherm occurred and the temperature was controlled at <30° C. using an ice bath. The mixture was stirred at 23° C. for 20 hours then poured into ice/water (1000 ml). After stirring for two hours the yellow solid was collected by suction filtration, washed with water and dried to yield 4-benzyloxy-3-methoxy-6-nitrobenzonitrile (10.1 g, 85% yield) as a yellow solid:

Workup

  1. customwas controlled at <30° C.
  2. stirringAfter stirring for two hours the yellow solid
  3. filtrationwas collected by suction filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-a9ed3b28c1dd4410a450a99aa08519fc
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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