Water → HCID 4324152, compound

HRID 1155735Notes

Reaction equation

HRID 1155735 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl[C:18]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:19]=1[C:20]#[N:21].O>CS(C)=O>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([O:14][C:18]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:19]=2[C:20]#[N:21])=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 132544-PhenoxyphenolHCID 14798Sodium HydroxideHCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 4324152HCID 4324152, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 5.71 g (0.0307 moles) of 4-phenoxyphenol dissolved in 150 ml of DMSO was added 1.23 g (0.0307 moles) of NaOH. The slurry was heated at 75° C. for 15 minutes and 5.04 g (0.0276 moles) of 2-chloro-5-nitrobenzonitrile was added and the mixture heated at 75° C. for 4 hrs. The reaction mixture was cooled and poured into water. The product was collected by filtration, washed well with water and dried. The crude product was dissolved in CH2CL2 and washed with 10% aqueous NaOH, water and dried (Na2SO4). Removal of solvent in vacuo afforded 8.0 g (87% yield) of product. Recrystallization from ethanol gave purified 2-(4-phenoxyphenoxy)-5-nitrobenzonitrile, mp 150°-151.5° C.

Workup

  1. temperaturethe mixture heated at 75° C. for 4 hrs
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was collected by filtration
  4. washwashed well with water
  5. customdried
  6. dissolutionThe crude product was dissolved in CH2CL2
  7. washwashed with 10% aqueous NaOH, water
  8. dry with materialdried (Na2SO4)
  9. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-f9e0b29400fc450f9447d5c83b57a28b
Source dataset
uspto-grants-1982_06
Patent number
US04332820

Reaction notes

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