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

Participants

Reaction Conditions

Reaction Steps

A solution of 1,4-cyclohexanedione monoethylene ketal (31.2 g, 200 mmole) in dry THF (250 ml) was added to a solution of 4-fluorophenylmagnesium bromide in dry THF at -60° C. The mixture was allowed to warm to 25° C. and quenched with saturated NH4Cl solution and extracted with ether. The extracts were dried with Na2SO4 and the solvent removed in vacuo. The residue was crystallized from hexane to give the product (89%, mp: 133°-135° C.). Calc'd for C14H17FO3 : C, 66.66%; H, 6.80%. Found: C, 66.54%; H, 7.12%.

Provenance & Evidence