Hydroquinone → 4-(5-Chloro-3-nitropyridin-2-yloxy)phenol

HRID 845696Notes

Reaction equation

[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([Cl:25])=[CH:18][N:17]=1>C(#N)C>[Cl:25][C:19]1[CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[C:16]([O:2][C:1]2[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=2)=[N:17][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 85.9 g (0.78 mole) of hydroquinone, 1200 ml of acetonitrile and 53.9 g (0.39 mole) of potassium carbonate is heated to 60° C., then a solution of 115.8 g (0.60 mole) of 2,5-dichloro-3-nitropyridine in 500 ml of acetonitrile is added dropwise over 6 hours and the mixture is stirred for 36 hours. The solvent is removed by distillation and the residue is poured into a mixture of ice-water and hydrochloric acid. After extraction with methylene chloride, the combined organic phases are dried over magnesium sulfate, treated with activated carbon, filtered and concentrated. The residue is purified by crystallisation in a mixture of hexane and ethyl acetate, affording 99 g (62% of theory) of 4-(5-chloro-3-nitropyridin-2-yloxy)phenol with a melting point of 125°-126° C.

Workup

customThe solvent is removed by distillation
additionthe residue is poured into a mixture of ice-water and hydrochloric acid
extractionAfter extraction with methylene chloride
dry with materialthe combined organic phases are dried over magnesium sulfate
additiontreated with activated carbon
filtrationfiltered
concentrationconcentrated
customThe residue is purified by crystallisation in a mixture of hexane and ethyl acetate

Sources & evidence

ORD record: ord-7579d0da3a734c0bafb0934b2e3c161f
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04759796

Reaction notes

Loading…