Water → Benzonitrile, 2-(4-chlorophenoxy)-5-nitro-

HRID 1155734Notes

Reaction equation

HRID 1155734 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[C:12]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=1[C:14]#[N:15].O>CS(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:13]=2[C:14]#[N:15])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 14798Sodium HydroxideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 514838Benzonitrile, 2-(4-chlorophenoxy)-5-nitro-Yield 92.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3.95 g (0.0307 moles) of 4-chlorophenol dissolved in 150 ml of DMSO was added 1.23 g (0.0307 moles) of NaOH. The slurry was heated at 60° C. for 15 minutes and 5.04 g (0.0276 moles) of 2-chloro-5-nitrobenzonitrile was added and the mixture was heated at 75° C. for 3 hrs. The reaction mixture was cooled and poured into water. The product was collected by filtration, washed well with water and dried, to produce 7.0 g of the product (92% yield). Recrystallization from ethanol afforded purified 2-(4-chlorophenoxy)-5-nitrobenzonitrile, mp 163°-164° C.

Workup

  1. temperaturethe mixture was heated at 75° C. for 3 hrs
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was collected by filtration
  4. washwashed well with water
  5. customdried

Sources & evidence

ORD record
ord-02be3259ac9b45029fa6d9574e2e216a
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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