Hydrochloric Acid → HCID 10171341, compound

Participants

Reaction Steps

Compound HA-3 (4-Butoxybenzohydroxamic Acid) was synthesised from methyl 4-butoxybenzoate. Hydroxylamine hydrochloride (6.95 g, 100 mmol) was dissolved in AR Grade methanol (20 mL) under Argon, then added to NaOMe (25% w/w in MeOH) 52.9 mL, 231 mmol) under Ar with ice cooling. A solution of methyl 4-butoxybenzoate (10.0 g, 48.0 mmol) in MeOH (50 mL) was then added, and the reaction stirred at room temperature under Ar. After 3 weeks, the reaction mixture was acidified to pH 6 with conc. HCl (caution!). The mixture was filtered and the filtrate evaporated to give a precipitate. This was extracted with CHCl3, the combined extracts dried (MgSO4) and the solvent evaporated. The residue was recrystallised from EtOH to give 4-butoxybenzohydroxamic acid as crystals, m.p. 152.6°-152.9° C. (8.25 g, 82%).

Provenance & Evidence