Water → HCID 4855228, compound

Participants

Reaction Steps

In 50 ml of dimethylsulfoxide, 12 g of hydroquinone monobenzyl ether, 8.2 g of 2-chloroquinoline and 8.3 g of potassium carbonate were dissolved and the mixture was heated at 150° to 160° C. for 4 hours to react them. After cooling, the reaction mixture was poured into water and the product was extracted with ether for several times and the ether layer was washed with an aqueous solution of sodium hydroxide and then with water and the ether layer was dehydrated over sodium sulfate. The solvent was distilled off. The resulting crude crystal was washed with diisopropyl ether to obtain 12 g (yield 75%) of 2-(4-benzyloxyphenoxy)quinoline. All of the intermediate was dissolved in 200 ml of a mixed solvent of tetrahydrofuran and ethanol (5:1) and 1.5 g of palladium-carbon type catalyst was added and 880 ml of hydrogen gas was fed into the mixture to carry out the hydrogenation at the atmospheric pressure. After the hydrogenation, the catalyst was separated by a suction filtration and the solvent was distilled off and the residue was washed with chloroform-n-hexane type solvent to obtain 6.3 g (yield 74%) of white crystal of 2-(4-hydroxyphenoxy)quinoline (m.p. 177° C.).

Provenance & Evidence