Water → 2-Methyl-3-(3-chloro-2-cyanophenoxy)-1-propene

HRID 233599

Reaktionsgleichung

Reaktionsgleichung von HRID 233599
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5].[CH3:11][C:12](=[CH2:15])[CH2:13][OH:14].[OH-].[K+].O>CS(C)=O>[CH3:15][C:12]([CH2:13][O:14][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[C:4]#[N:5])=[CH2:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 3031DichlobenilHCID 10557Methallyl alcoholHCID 14797Potassium Hydroxide

Produkt 1

HCID 541242722-Methyl-3-(3-chloro-2-cyanophenoxy)-1-propeneAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 30.0 grams (0.174 mole) of 2,6-dichlorobenzonitrile and 14.7 mL (0.174 mole) of 2-methyl-2-propen-1-ol in 200 mL of dimethyl sulfoxide is stirred, and 12.7 grams (0.191 mole) of 85% potassium hydroxide is added portionwise during a 5 minute period. During the addition, the reaction mixture temperature rises from 20° C. to about 35° C. Upon completion of the addition, the reaction mixture is stirred at ambient temperature for about 18 hours. After this time the reaction mixture is poured into 600 mL of water. The mixture is filtered to collect a solid. The solid is washed with water and dried under vacuum, yielding 33.9 grams of 2-methyl-3-(3-chloro-2-cyanophenoxy)-1-propene. The NMR spectrum is consistent with the proposed structure.

Aufarbeitung

  1. additionDuring the addition
  2. customrises from 20° C. to about 35° C
  3. additionUpon completion of the addition
  4. filtrationThe mixture is filtered
  5. customto collect a solid
  6. washThe solid is washed with water
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f0700d90ff024e4d9170ebd229069fce
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05593998

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