Catechol → HCID 15917385, compound

HRID 1758136Notes

Reaction equation

HRID 1758136 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Cl[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][N:11]=1>C(Cl)Cl>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:2][C:1]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])=[N:11][CH:12]=1

Participants

4

Reactant 2

HCID 289CatecholHCID 276852,5-Dichloropyridine

Product 1

HCID 15917385HCID 15917385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, a mixture of 15.0 grams (0.136 mole) of catechol, and 22.0 grams of 2,5-dichloropyridine was heated as a melt at 140°-150° for 12 hours. The resulting black residue was dissolved in a minimum amount of methylene chloride, i.e., about 50 ml, chromatographed through a silica gel column using methylene chloride as the eluent. The 2-(5-chloropyridin-2-yloxy)phenol was isolated in the latter fraction, whereas starting material 2,5-dichloropyridine eluted with the solvent front. Yield 8.0 grams, m.p. 97°-100°; NMR (CDCl3): δ6.70-7.70 (m's, ArH and OH), 8.0 (d, ArH); ir (Nujol): 3.20-2.80 (OH), 6.30 (C=N), 13.30 microns.

Workup

  1. temperaturewas heated as a melt at 140°-150° for 12 hours
  2. customchromatographed through a silica gel column

Sources & evidence

ORD record
ord-da7ed16a0e67440fb8fb119f75033a49
Source dataset
uspto-grants-1983_02
Patent number
US04371736

Reaction notes

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