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

HRID 52647

Reaction equation

HRID 52647 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 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.

Workup

  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

Sources & evidence

ORD record
ord-cafb03d01c164218a99c58a85408b370
Source dataset
uspto-grants-1997_04
Patent number
US05616718

Linked notes

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