1-[1-(difluoromethoxy)naphthalen-2-yl]ethanone

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g of 1-hydroxy-2-acetylnaphthalene are dissolved in 60 ml of dioxane, and 30 ml of 30% sodium hydroxide solution are added. At a temperature of from 70° C. to 80° C., difluorochloromethane (Freon 22) is introduced until no further absorption is observed. The dioxane phase is then decanted, the NaOH phase is washed with dioxane, the dioxane phase is decanted, and the combined dioxane solutions are largely concentrated in vacuo using a rotary evaporator. Water is added to the residue, the mixture is extracted several times with diethyl ether, and the diethyl ether solution is dried over Na2SO4, filtered and concentrated by evaporation. The residue is recrystallised from diethyl ether/hexane. Yield: 4 g, m.p. 80°-81° C. The dioxane phase is then decanted the NaOH phase is washed with dioxane the dioxane phase is decanted the combined dioxane solutions are largely concentrated in vacuo a rotary evaporator Water is added to the residue the mixture is extracted several times with diethyl ether the diethyl ether solution is dried over Na2SO4 filtered concentrated by evaporation The residue is recrystallised from diethyl ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g of 1-hydroxy-2-acetylnaphthalene are dissolved in 60 ml of dioxane, and 30 ml of 30% sodium hydroxide solution are added. At a temperature of from 70° C. to 80° C., difluorochloromethane (Freon 22) is introduced until no further absorption is observed. The dioxane phase is then decanted, the NaOH phase is washed with dioxane, the dioxane phase is decanted, and the combined dioxane solutions are largely concentrated in vacuo using a rotary evaporator. Water is added to the residue, the mixture is extracted several times with diethyl ether, and the diethyl ether solution is dried over Na2SO4, filtered and concentrated by evaporation. The residue is recrystallised from diethyl ether/hexane. Yield: 4 g, m.p. 80°-81° C. The dioxane phase is then decanted the NaOH phase is washed with dioxane the dioxane phase is decanted the combined dioxane solutions are largely concentrated in vacuo a rotary evaporator Water is added to the residue the mixture is extracted several times with diethyl ether the diethyl ether solution is dried over Na2SO4 filtered concentrated by evaporation The residue is recrystallised from diethyl ether/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 10 g of 1-hydroxy-2-acetylnaphthalene are dissolved in 60 ml of dioxane, and 30 ml of 30% sodium hydroxide solution are added. At a temperature of from 70° C. to 80° C., difluorochloromethane (Freon 22) is introduced until no further absorption is observed. The dioxane phase is then decanted, the NaOH phase is washed with dioxane, the dioxane phase is decanted, and the combined dioxane solutions are largely concentrated in vacuo using a rotary evaporator. Water is added to the residue, the mixture is extracted several times with diethyl ether, and the diethyl ether solution is dried over Na2SO4, filtered and concentrated by evaporation. The residue is recrystallised from diethyl ether/hexane. Yield: 4 g, m.p. 80°-81° C. The dioxane phase is then decanted the NaOH phase is washed with dioxane the dioxane phase is decanted the combined dioxane solutions are largely concentrated in vacuo a rotary evaporator Water is added to the residue the mixture is extracted several times with diethyl ether the diethyl ether solution is dried over Na2SO4 filtered concentrated by evaporation The residue is recrystallised from diethyl ether/hexane