Water → HCID 67546509, compound

Participants

Reaction Steps

A mixture of orthophosphoric acid (147.5 mL) and demineralized water (29.5 mL) is added to a stirred toluene solution (300 mL) of 3-hydroxymethyl-4-(1-hydroxy-1-methylethyl)benzonitrile (29.5 g, 0.154 mol) at 0-5° C. The reaction mixture is stirred at room temperature for 3.0 hrs. The toluene layer is separated and the aqueous layer is extracted with toluene (3×50 mL). Combined organic layers are washed with saturated sodium bicarbonate solution (1×40 mL) followed by demineralized water (1×40 mL). Evaporation of the toluene layer under reduced pressure gives a viscous liquid which is purified by column chromatography (silica gel 230-400 mesh,) to give 1,1-dimethyl-1,3-dihydro-2-benzofuran-5-carbonitrile.

Provenance & Evidence