Sodium Carbonate → 3-Allyl-4-hydroxybenzamidoxime

Reaction equation

[CH2:1]([C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[OH:12])[CH:2]=[CH2:3].Cl.[NH2:14][OH:15].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[OH:12])[C:10](=[N:14][OH:15])[NH2:11])[CH:2]=[CH2:3]

Participants

Procedure

A solution of 2-allyl-4-cyanophenol (5.5 g), hydroxylamine hydrochloride (8.5 g) and sodium carbonate (6.1 g) in aqueous ethanol was heated at reflux for 3 hours. The solution was cooled to ambient temperature and the ethanol was removed by evaporation. The solid was collected by filtration, dissolved in ethanol and the solution was filtered. The filtrate was evaporated and the residual solid was triturated with hexane to give 3-allyl-4-hydroxybenzamidoxime as a solid (5.5 g), m.p. 144° C.