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

HRID 371035Notes

Reaction equation

HRID 371035 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 chromatographed 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
  6. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-4f564ecb133e48fe8515d942dea3c6d6
Source dataset
uspto-grants-1985_07
Patent number
US04529438

Reaction notes

Loading…