N-(1,4-dioxaspiro[4.5]decan-8-ylidene)hydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1,4-dioxaspiro[4.5]decan-8-one oxime (68 g, 400 mmol) in ethanol (200 mL) was added Raney Nickel as a suspension in ethanol (52 mL). The resulting mixture was shaken at 50 psi of hydrogen for 18 hours. The reaction was filtered and concentrated in vacuo to give 57.5g of 1,4-dioxaspiro[4.5]dec-8-ylamine. The reaction was filtered concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 1,4-dioxaspiro[4.5]decan-8-one (50.3 g, 322.1 mmol) and hydroxylamine hydrochloride (89.5 g, 100.3 mmol) in water (450 mL) was added portionwise sodium carbonate (102.4 g, 966.2 mmol). The reaction mixture was stirred for 40 minutes at room temperature then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give 68.2 g of crude 1,4-dioxaspiro[4.5]decan-8-one oxime. then extracted with ethyl acetate The organic layer was washed with brine dried over magnesium sulfate filtered concentrated in vacuo