1,4-Dioxaspiro[4.5]decan-8-one → 1,4-Dioxaspiro(4.5)decan-8-ol

Participants

Reaction Conditions

Reaction Steps

Into a 250 ml round bottom flask is weighed 20 g of 1,4-dioxa-spiro[4.5]decan-8-one (128 mmol) and dissolved in 200 ml of methanol to give a pale yellow solution. The solution is cooled to 5° C. and sodium borohydride (4 g, 106 mmol) is added portionwise keeping the temperature below 20° C. Once the addition is complete the solution was stirred at room temperature for 3 hours. The reaction is evaporated to one third volume and then diluted with water, acidified carefully with 0.5 M aqueous hydrochloric acid, and extracted with diethyl ether (2×100 ml). The combined organics extracts are dried over magnesium sulphate, filtered and evaporated to give 1,4-dioxa-spiro[4.5]decan-8-ol (12.2 g).

Provenance & Evidence