Nitric Acid → 4-(2-Nitrophenyl)butyronitrile

HRID 1198542Notes

Reaction equation

HRID 1198542 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13]>>[N+:12]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH2:7][CH2:8][CH2:9][C:10]#[N:11])([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 74897Benzenebutanenitrile

Product 1

HCID 112177214-(2-Nitrophenyl)butyronitrile

Procedure

4-Phenylbutyronitrile (12.7 g) was added dropwise to stirred concentrated nitric acid (55 ml) at 5°-10° C. and the mixture was stirred for 2 hours at 20°-25° C. The deep yellow solution was poured onto ice and extracted with dichloromethane. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:4) to isolate the minor product.

Workup

  1. additionThe deep yellow solution was poured onto ice
  2. extractionextracted with dichloromethane
  3. customThe extract was dried
  4. customevaporated
  5. customthe residue was chromatographed on silica in ethyl acetate-hexane (1:4)
  6. customto isolate the minor product

Sources & evidence

ORD record
ord-aa8b86666141487e8d6fcbc603644825
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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