Sodium Methoxide → HCID 13042037, compound

Participants

Reaction Steps

A 1,000-milliliter flask equipped with a reflux condenser and a magnetic stirring bar was charged with 24.1 grams (0.13 mole) of α-methyl-3-nitrobenzyl chloride in 400 milliliters of methyl alcohol. To this stirred solution was added 8.1 grams (0.15 mole) of sodium methoxide. The reaction mixture was heated to reflux and maintained at reflux for 26 hours. Since some traces of α-methyl-3-nitrobenzyl chloride were present (as indicated by a thin layer chromatograph test), an additional 5.4 grams (0.1 mole) of sodium methoxide was added and the reaction was again heated to reflux and maintained at reflux for 49 hours. The reaction mixture was then cooled and concentrated on a rotary evaporator at 55° C. The residue was taken up with 200 milliliters of methylene chloride, transferred to a separatory funnel and washed consecutively with 100 milliliter portions each of water, 1 Normal hydrochloric acid, water, 1 Normal sodium hydroxide, and water, respectively. The organic layer was separated, dried over magnesium sulfate and concentrated on a rotary evaporator at 55° C., leaving a dark liquid residue. The dark liquid was charged to a distillation flask and distilled at a pressure of 1.8 millimeters of mercury. A main fraction (14.98 grams) was collected, said fraction having a boiling point of 106° C.-112° C. at 1.8 mm Hg pressure. This main fraction was identified by NMR spectroscopy as 1-(1-methoxyeth-1-yl)-3-nitrobenzene.

Provenance & Evidence