Ammonia → HCID 21504103, compound

Participants

Reaction Steps

Methyl (5-methoxynaphth-2-yl)ketone (0.25 moles) and phosphorus pentachloride (0.31 moles) are placed in a 3-neck flask equipped with a mechanical stirrer, a condenser connected to a nitrogen inlet, and a thermometer. The mixture is stirred at 33°-35° C for 3 days. The cooled reaction mixture is poured onto 800 g of ice and extracted with 3 × 500 ml of ether. The ether fraction is washed with 2 × 100 ml water 4 × 100 ml of 5% sodium hydroxide, 3 × 50 ml water, 2 × 50 ml of saturated saline and dried over sodium sulfate. The ether is removed to give the chlorinated intermediate. The intermediate is dissolved in anhydrous THF (200 ml) and is added dropwise to a freshly prepared solution of sodamide in liquid ammonia, using a dry-ice condenser. The reaction mixture is allowed to stir at room temperature overnight; then, it is poured into 50 ml of water and 500 ml of ether. The ether fraction is washed with 3 × 50 ml water and solvent gives a residue which is distilled to give 2-ethynyl-5-methoxynaphthalene.

Provenance & Evidence