Chloroacetonitrile → (4-(4-(Methylsulfonyl)phenoxy)phenoxy)acetonitrile

HRID 2164644

Reaktionsgleichung

Reaktionsgleichung von HRID 2164644
[CH3:1][S:2]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Cl[CH2:20][C:21]#[N:22].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>C(#N)C>[CH3:1][S:2]([C:5]1[CH:18]=[CH:17][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:20][C:21]#[N:22])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Komponenten

6

Edukt 4

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 514882Phenol, 4-(4-(methylsulfonyl)phenoxy)-

Produkt 1

HCID 13078520(4-(4-(Methylsulfonyl)phenoxy)phenoxy)acetonitrileAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 5.29 g (0.0200 mole) of 4-(4-(methylsulfonyl)phenoxy)phenol and 1.51 g (0.0200 mole) of 2-chloroacetonitrile in 100 ml of acetonitrile was added 3.0 g (0.0220 mole) of K2CO3. The mixture was heated at reflux for 3.5 hrs and cooled. The mixture was poured into aqueous NaOH and the product extracted from the mixture with CH2Cl2. The organic layer was extracted with aqueous NaOH, water and dried (Na2SO4). Removal of solvent in vacuo afforded 5.6 g (92.4% yield) of product. Recrystallization from ethanol followed by washing with aqueous NaOH and water afforded purified (4-(4-(methylsulfonyl)phenoxy)phenoxy)acetonitrile, mp 114°-115.5° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3.5 hrs
  3. temperaturecooled
  4. extractionthe product extracted from the mixture with CH2Cl2
  5. extractionThe organic layer was extracted with aqueous NaOH, water
  6. dry with materialdried (Na2SO4)
  7. customRemoval of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-36a243dff25145769df82ed4d451001c
Quelldatensatz
uspto-grants-1985_03
Patentnummer
US04505929

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