Isopropanol → HCID 13042036, compound

Participants

Reaction Steps

A 500-milliliter flask equipped with a reflux condenser and a magnetic stirring bar was charged with 17.1 grams (0.1 mole) of 3-nitrobenzyl chloride in 250 milliliters of isopropanol. To this stirred solution was added 6.43 grams (0.1 mole) of potassium hydroxide in 25 milliliters of water. The reaction mixture was heated to reflux and maintained at reflux for 23 hours. The reaction mixture was then cooled, filtered, and the filtrate was concentrated on a rotary evaporator at 55° C. The residue was slurried with 300 milliliters of methylene chloride and transferred to a separatory funnel wherein it was washed consecutively with 100 milliliter portions of 1 Normal hydrochloric acid, water, 1 Normal sodium hydroxide, and water, respectively. The organic phase was separated, dried over magnesium sulfate, and concentrated on a rotary evaporator at 55° C., leaving a dark brown liquid. The dark brown liquid was charged to a distillation flask and distilled at a pressure of 2.4 millimeters of mercury. A main fraction (8.2 grams) was collected, said fraction having a boiling point of 123°-125° C. at 2.4 mm Hg pressure. This main fraction was identified by NMR spectroscopy as 1-(isopropoxymethyl)-3-nitrobenzene.

Provenance & Evidence