Hydrochloric Acid → 2-(Naphthalen-1-yl)propane-1,3-diol

Participants

Reaction Steps

50 g (175 mmol) of diethyl 2-(naphthalen-1-yl)propanedioate in 310 ml of dioxane and 300 ml of water are stirred at ambient temperature; an excess (2.2 mol, or 84 g) of sodium borohydride is then added in portions; the mixture is stirred for 8 h, and the products are left in contact for 2 days. The mixture is then hydrolysed, with stirring, while introducing crushed ice and 3N hydrochloric acid until an acidic pH is obtained. The mixture is extracted with diethyl ether, the organic phase is evaporated, and the residual oil is purified by chromatography on a silica gel column eluted with ethyl acetate. After evaporation and drying at 40° C. in the presence of phosphorus pentoxide, 18.5 g (91 mmol) of product are isolated. Melting point: 58-60° C.

Provenance & Evidence