Water → 1-(1,4-Dioxaspiro[4.5]dec-8-yl)-2-phenoxyethanol

Participants

Reaction Steps

A 60% strength dispersion of sodium hydride in mineral oil (834 mg, 20.7 mmol) was taken up in anhydrous N,N-dimethylformamide (10 ml), and phenol (1.96 g, 20.8 mmol) was added. The mixture was stirred at room temperature for 15 min and a solution of 8-oxiranyl-1,4-dioxaspiro[4.5]decane (2.62 g, content approx. 30%, approx. 4 mmol) in N,N-dimethylformamide (6 ml) was then added. The reaction mixture was stirred at 120° C. for 5.5 h and then cooled to room temperature, water (1 ml) was added and the mixture was concentrated in vacuo. Toluene was repeatedly added to the residue and the mixture was concentrated again in vacuo each time. The crude product (2.9 g) was purified by flash chromatography (200 g, 20×5.6 cm) with cyclohexane/ethyl acetate (4:1).

Provenance & Evidence