Sodium Hydroxide → 2,6-Diethyl-2,3,6-trimethylpiperidin-4-ol

Participants

Reaction Steps

In a 2-liter, 3-necked flask equipped with a stirrer, condenser, thermometer and nitrogen inlet were placed 197.3 g. (1.0 moles) of 2,6-diethyl-2,3,6-trimethylpiperidin-4-one, 500 ml of 2N sodium hydroxide and 500 ml of absolute ethanol. To the stirred reaction mixture, maintained under nitrogen, was added portionwise 18.92 m (0.5 moles) of sodium borohydride over a 11/2 hour period. The reaction mixture was then stirred overnight at room temperature. The reaction mixture was decanted into a 4-liter separatory funnel and 2 liters of water were added. The aqueous layer was separated and the organic layer diluted with 500 ml of ether. The ether solution was washed with 2×1 l water. The first aqueous layer was extracted with 2×50 ml of ether, then the combined ether extracts were washed with 500 ml of water. The ether layers were combined, dried over 4A molecular sieves and evaporated under reduced pressure, giving 187.4 g of the desired 2,6-diethyl-2,3,6-trimethylpiperidin-4-ol which was purified further by vacuum distillation, b.p. 111°-115°/6 mm.

Provenance & Evidence