Hydrochloric Acid → HCID 13565961, compound

Participants

Reaction Steps

To a mixture of 12.7 g of 3,4-dibenzyloxybenzaldehyde and 150 ml of tetrahydrofuran was added dropwise an ether solution of Grignard reagent prepared from 10.4 g of 2-methyl-2-(6-bromohexyl)-1,3-dioxolane and 1.1 g of magnesium at a temperature below 5° C. After stirring the mixture for 2 hours at room temperature, water was added to the mixture and acidifying the mixture by the addition of diluted hydrochloric acid, the reaction mixture thus obtained was extracted with toluene. The extract was washed with water, dried by anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue were added 300 ml of acetone and 0.1 g of p-toluenesulfonic acid, the mixture was stirred overnight at room temperature and concentrated under reduced pressure. The residue was extracted with toluene and the extract was washed with an aqueous 5% sodium hydrogencarbonate solution, washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide an oily product. The product was applied to silica gel (500 ml) column chromatography and eluted with a mixture of toluene and ethyl acetate (19:1) to provide 4.4 g of 1-(3,4-dibenzyloxyphenyl)-1,8-nonanedione. Melting point 64°-66° C.

Provenance & Evidence