Catechol → HCID 15917385, compound

Participants

Reaction Steps

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.

Provenance & Evidence