Hydrochloric Acid → N-(4-n-pentyloxybenzoyl)-N,O-dimethylhydroxylamine

Beteiligte Stoffe

Reaktionsschritte

To a suspension of 4-n-pentyloxybenzoic acid (5.0 g) in toluene was added oxalyl chloride (15 ml) and N,N-dimethylformamide (0.1 ml) and the mixture was stirred for 2 hours at room temperature. The solvents were evaporated under reduced pressure to give crude 4-n-pentyloxybenzoyl chloride. To a suspension of N,O-dimethylhydroxylamine a hydrochloride (3.51 g) and pyridine (5.82 ml) in tetrahydrofuran (25 ml) was added the solution of crude 4-n-pentyloxybenzoyl chloride in tetrahydrofuran (25 ml) dropwise at 0° C. and the mixture was stirred for 3 hours at room temperature. To the reaction mixture 1N HCl was added and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure to give N-(4-n-pentyloxybenzoyl)-N,O-dimethylhydroxylamine (4.63 g).

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