delta-Gluconolactone → (4-(Benzyloxy)phenyl)hydrazine monohydrochloride

Participants

Reaction Conditions

Reaction Steps

To a slurry of 4-benzyloxyaniline (250 g) and ethanol 300 ml) in 30% HCl (350 ml) and 37% HCl (150 ml) was added a solution of sodium nitrite (77 g) in water (350 ml), while maintaining the temperature between -8 and -2° C. The reaction was stirred for an additional four hours at -2° C. A solution of tin (II) chloride dihydrate (710 g) in 30% HCl (770 ml) was added slowly followed by d-gluconic acid lactone (575 g), and the resulting white suspension was cooled overnight. The crude product was collected by vacuum filtration and washed with 1 N hydrochloric acid, ether, and vacuum dried to give 248.9 g of the desired product, m.p. 173-174° C.

Provenance & Evidence