Ammonia → HCID 13533745, compound

Participants

Reaction Steps

To a stirred refluxing mixture of 600 ml. of dry ether and 1600 ml of liquid ammonia was added 136 g of p-ethylanisole. After 15 minutes, there was added portionwise, at -35° to -32° C., 26.4 g of lithium ribbon over 0.5-1 hour. After an additional 15 minutes, 193 g of dry ethanol was added dropwise at -35° to -32° C. Stirring was continued until the blue color disappeared, and the ammonia was allowed to evaporate on standing overnight. The residue was poured into 1 l of ice water and extracted twice with ether. The combined ether extracts concentrated to a volume of about 300 ml was stirred with 250 ml of water containing 46 g of oxalic acid overnight at ambient temperature. This mixture was diluted with 1 liter of water and extracted twice with ether. The combined ether extracts was washed with 5% sodium bicarbonate and then with water. After drying, the ether solution was vacuumconcentrated to a residue of 104.4 g of desired product; it was 94% pure by GLC analysis and used without distillation.

Provenance & Evidence