Hydrochloric Acid → 5-Chloro-2-(3-hydroxyphenoxy)benzonitrile

HRID 1074879Notes

Reaction equation

HRID 1074879 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[OH-].[K+].Cl[C:12]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:13]=1[C:14]#[N:15].Cl>CS(C)=O>[C:14]([C:13]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:12]=1[O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1)#[N:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 14797Potassium HydroxideHCID 890002,5-Dichlorobenzonitrile

Product 1

HCID 204951765-Chloro-2-(3-hydroxyphenoxy)benzonitrileYield 67.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

66 g of resorcinol are added to 220 ml of dimethyl sulphoxide. With stirring, 37.4 g of potassium hydroxide (powder) are added, whereupon the temperature rises to 55° C. The mixture is kept for 30 minutes at 60° C. and the 51.6 g of 2,5-dichlorobenzonitrile are added in portions. The reaction mixture is then stirred for 7 hours at 90° C. and, after cooling, poured into ice-water. The pH is adjusted to 6 with conc. hydrochloric acid and initially a brown oil precipitates, which soon becomes crystalline. Crystallisation from ethanol/-water yields 49.6 g of 3-(2'-cyano-4'-chlorophenoxy)-phenol with a melting point of 118°-120° C.

Workup

  1. customrises to 55° C
  2. stirringThe reaction mixture is then stirred for 7 hours at 90° C.
  3. temperatureafter cooling
  4. custominitially a brown oil precipitates
  5. customCrystallisation from ethanol/-water

Sources & evidence

ORD record
ord-3a00aab288f8408e9538f02bac6d9d3e
Source dataset
uspto-grants-1983_07
Patent number
US04394327

Reaction notes

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