p-Toluenesulfonic acid → 8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

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Reaction Steps

A mixture of 8-(4-fluorophenyl)-1,4-dioxaspiro[4.5]decan-8-ol (2.0 g, 7.9 mmole) and a catalytic amount of p-toluenesulfonic acid in 50 ml toluene was heated at reflux for 1.5 hr. The mixture was cooled and washed with saturated sodium bicarbonate solution. The toluene was removed in vacuo and the residue recrystallized from hexane to give the product (81%, mp: 84-85° C.). Calc'd for C14H15FO2 : C, 71.78%; H, 6.46%. Found: C, 71.33%; H, 6.33%.

Provenance & Evidence