Hydrochloric Acid → 4-(3,5-Dichloro-pyridin-2-yloxy)-phenol

HRID 1248542Notes

Reaction equation

HRID 1248542 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[C:10]1([CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=1)[OH:11].[OH-].[K+].Cl>O.CS(C)=O>[Cl:8][C:7]1[C:2]([O:11][C:10]2[CH:17]=[CH:16][C:14]([OH:15])=[CH:13][CH:12]=2)=[N:3][CH:4]=[C:5]([Cl:9])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 14797Potassium HydroxideHCID 27666Pyridine, 2,3,5-trichloro-

Product 1

HCID 6208804-(3,5-Dichloro-pyridin-2-yloxy)-phenol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 2,3,5-trichloropyridine (2.5 g, 13.7 mm), hydroquinone (3.02 g, 27.4 mm), KOH (3.07 g, 54.8 mm) and DMSO (10 ml) is heated to 160° for 3 hours. The mixture is poured into water, acidified with dilute HCl and extracted with ether. The ethereal solution is washed, dried and evaporated to dryness. The crude product is chromotographed on silica gel to give crystalline 4-(3,5-dichloropyridyloxy) phenol.

Workup

  1. temperatureis heated to 160° for 3 hours
  2. extractionextracted with ether
  3. washThe ethereal solution is washed
  4. customdried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f2f9f0dc6f644998907e4eea3a083292
Source dataset
uspto-grants-1985_06
Patent number
US04525205

Reaction notes

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