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

HRID 1003998Notes

Reaction equation

HRID 1003998 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:12]#[N:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:19]([O-])([OH:21])=[O:20].O>C(O)(=O)C>[CH2:1]([O:8][C:9]1[C:16]([O:17][CH3:18])=[CH:15][C:14]([N+:19]([O-:21])=[O:20])=[C:11]([CH:10]=1)[C:12]#[N:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 27522763-(Benzyloxy)-4-methoxybenzonitrile

Product 1

HCID 110333845-(Benzyloxy)-4-methoxy-2-nitrobenzonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-benzyloxy-4-methoxybenzonitrile (43.8 g, 0.18 mol) in glacial acetic acid (87 ml) was added dropwise to concentrated nitric acid (70% w/w, 244 ml) with periodic cooling to maintain the reaction temperature below 30° C. Once the addition was complete, the reaction was stirred for a further 30 minutes, after which time the mixture was poured into water (11) and stirred for 30 minutes. The resulting precipitate was isolated by filtration, washed with water and dried under reduced pressure at 50° C. to afford the subtitle compound as a white solid (35.1 g, 68%). Rf 0.70 (EtOAc:hexane 1:1, v/v).

Workup

  1. temperaturewith periodic cooling
  2. temperatureto maintain the reaction temperature below 30° C
  3. additionOnce the addition
  4. stirringstirred for 30 minutes
  5. customThe resulting precipitate was isolated by filtration
  6. washwashed with water
  7. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-135a3717637a440193c0b4d4ffff8d6a
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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