Ammonia → HCID 13533745, compound

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 vacuum-concentrated to a residue of 104.4 g of desired product; it was 94% pure by GLC analysis and used without distillation.

1. temperatureTo a stirred refluxing
2. additionmixture of 600 ml
3. additionthere was added portionwise, at -35° to -32° C.
4. waitAfter an additional 15 minutes
5. customto evaporate
6. waiton standing overnight
7. additionThe residue was poured into 1 l of ice water
8. extractionextracted twice with ether
9. concentrationThe combined ether extracts concentrated to a volume of about 300 ml
10. stirringwas stirred with 250 ml of water containing 46 g of oxalic acid overnight at ambient temperature
11. additionThis mixture was diluted with 1 liter of water
12. extractionextracted twice with ether
13. washThe combined ether extracts was washed with 5% sodium bicarbonate
14. customAfter drying
15. concentrationthe ether solution was vacuum-concentrated to a residue of 104.4 g of desired product
16. distillationused without distillation

ORD record

ord-dbf56458e7d44c3a9755a73e05d17886

Source dataset

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04542244