4-Nitrophenol → 4-Nitrophenoxyacetonitrile

HRID 1962252Notes

Reaction equation

HRID 1962252 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:12][C:13]#[N:14].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[C:13]([CH2:12][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)#[N:14]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 1418544-Nitrophenoxyacetonitrile

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

4-Nitrophenol (10 g), bromoacetonitrile (6 mL) and K2CO3 (15 g) were suspended in acetone (100 mL). The yellow solution was stirred at rt overnight. The reaction mixture was diluted with water (100 mL) and acetone was removed under reduced pressure. The light-yellow precipitate was collected by filtration, washed with water and dried to give O-cyanomethyl-4-nitrophenol.

Workup

  1. customwas removed under reduced pressure
  2. filtrationThe light-yellow precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-0b3e1c6377c1423aa0bc3df85194ae18
Source dataset
uspto-grants-2013_04
Patent number
US08415365B2

Reaction notes

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