Hydrochloric Acid → HCID 5168935, compound

Participants

Reaction Steps

Hydroxylamine hydrochloride (17.4 g, 250 mmol.) was dissolved in AR Grade methanol (50 mL) under argon, then added to NaOMe (25% w/w in MeOH) 132 mL, 580 mmol) under argon with ice cooling. A solution of methyl 4-pentylbenzoate, prepared above (25.15 g. 123 mmol) in methanol was then added, and the reaction stirred at room temperature under N2 for 3 days. 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-pentylbenzohydroxamic acid acid as crystals, m.p. 89.9°-90.1° C. (12.35 g, 49%).

Provenance & Evidence