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., a 26.4 g quantity 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 were 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. additionthere was added portionwise, at -35 ° to -32° C.
3. waitAfter an additional 15 minutes
4. customto evaporate
5. waiton standing overnight
6. additionThe residue was poured into 1 l of ice water
7. extractionextracted twice with ether
8. concentrationThe combined ether extracts concentrated to a volume of about 300 ml
9. stirringwas stirred with 250 ml of water containing 46 g of oxalic acid overnight at ambient temperature
10. additionThis mixture was diluted with 1 liter of water
11. extractionextracted twice with ether
12. washThe combined ether extracts were washed with 5% sodium bicarbonate
13. customAfter drying
14. concentrationthe ether solution was vacuum-concentrated to a residue of 104.4 g of desired product
15. distillationused without distillation

ORD record

ord-f08900ba03d640f5a980485667e536d9

Source dataset

uspto-grants-1984_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04487945