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

HRID 249197Notes

Reaction equation

HRID 249197 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]>CS(C)=O.O.C1OCCOCCOCCOCCOCCOC1>[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

6

Reactant 2

HCID 785HydroquinoneHCID 27666Pyridine, 2,3,5-trichloro-

Product 1

HCID 6208804-(3,5-Dichloro-pyridin-2-yloxy)-phenolYield 48.5%

Reagents, catalysts & solvents 3

HCID 2855718-Crown-6CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

2,3,5-Trichloropyridine (69.32 g, 0.38 mol) and 18-crown-6 (4.0 g, 0.015 mol) are added to a mixture of the dipotassium salt of hydroquinone (prepared from hydroquinone (44.0 g, 0.4 mol) and potassium hydroxide (45.0 g, 0.8 mol)) in dimethyl sulfoxide (700 mL). The reaction mixture is stirred overnight at room temperature, heated at 60° C. for 21/2 hours, diluted with water and extracted with ether. The combined organic extracts are washed with water, treated with charcoal, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain the title product as a white solid (47.23 g, mp 122°-123.5° C.)

Workup

  1. temperatureheated at 60° C. for 21/2 hours
  2. extractionextracted with ether
  3. washThe combined organic extracts are washed with water
  4. additiontreated with charcoal
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b83ad9e263e941e281837bdecdd8640c
Source dataset
uspto-grants-1993_05
Patent number
US05213606

Reaction notes

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