Methanol → HCID 18429663, compound

Participants

Reaction Steps

Then, 9.1 g of N-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)-phenoxy)propyloxy)phthalimide was added to 150 ml of methanol, to which 1.9 g of hydrazine hydrate was added. The reaction mixture was stirred for 1 hour with heating under reflux, and returned to room temperature. To the reaction mixture was added 50 ml of water, from which the methanol was evaporated under reduced pressure. Further added were 15 ml of concentrated hydrochloric acid and 25 ml of water. The reaction mixture was stirred for 30 minutes with heating under reflux, returned to room temperature, and filtered. The crystals collected by filtration were added to 10% aqueous sodium hydrogencarbonate solution, and extracted with diethyl ether. The diethyl ether layer was washed with 10% aqueous sodium hydrogencarbonate solution and water. To this diethyl ether layer was added 3 ml of concentrated hydrochloric acid, and the mixture was concentrated and the dried, which afforded 6.8 g (yield, 92%) of O-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyl)hydroxylamine hydrochloride, m.p., 171.8° C.

Provenance & Evidence