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

HRID 896249Notes

Reaction equation

HRID 896249 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:19]([O-])([OH:21])=[O:20].[OH-].[K+]>C(O)(=O)C>[N+:19]([C:15]1[CH:16]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10]([O:17][CH3:18])=[CH:11][C:12]=1[C:13]#[N:14])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14797Potassium HydroxideHCID 7937714-Benzyloxy-3-methoxy-benzonitrile

Product 1

HCID 116736184-(Benzyloxy)-5-methoxy-2-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-benzyloxy-3-methoxybenzonitrile (4.78 g, 20 mmol) in acetic acid (10 ml) was slowly added to nitric acid (25 ml) at 20° C. to 30° C. The mixture was stirred at room temperature for 6 hours, basified (pH 10-11) with cooling (KOH 10N), extracted with methylene chloride, dried over MgSO4 evaporated. The solid was recristallysed in hot EtOAc, a yellow solid of title compound was obtained (3.62 g, 64%).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-e617e8aafd544db5975afef715b40ad1
Source dataset
uspto-grants-2005_07
Patent number
US06919338B2

Reaction notes

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