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

HRID 1078232Notes

Reaction equation

HRID 1078232 reaction equation
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]

Participants

6

Reactant 4

HCID 962WaterHCID 3031DichlobenilHCID 10557Methallyl alcoholHCID 14797Potassium Hydroxide

Product 1

HCID 541242722-Methyl-3-(3-chloro-2-cyanophenoxy)-1-propeneYield 93.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ec4c245975cd4608b8bda6fd0b901015
Source dataset
uspto-grants-1996_08
Patent number
US05547954

Reaction notes

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