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

HRID 363780

Reaktionsgleichung

Reaktionsgleichung von HRID 363780
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 was stirred, and 12.7 grams (0.191 mole) of 85% potassium hydroxide was added portionwise during a 5 minute period. During the addition, the reaction mixture temperature rose from 20° C. to about 35° C. Upon completion of the addition, the reaction mixture was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was poured into 600 mL of water. The mixture was filtered to collect a solid. The solid was washed with water and dried under vacuum, yielding 33.9 grams of 2-methyl-3-(3-chloro-2-cyanophenoxy)-1-propene. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ee3b22281e484de2b1a6cd6a549e9814
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874579

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