Sulfuric Acid → HCID 20135589, compound

To a stirred mixture of 52.5 g. (0.253 mole) of 4-(4-methoxyphenyl)-1,1-dimethylbutyl alcohol, and 44.5 g. (0.685 mole) of powdered potassium cyanide in 200 ml. of n-butyl ether at 60° C. was added dropwise over 1 hour 80 ml. of concentrated sulfuric acid. The temperature was maintained at 60°-65° C. throughout the addition and stirring was continued at 50°-55° C. an additional hour after the addition was complete. The reaction mixture was then poured into 850 ml. of ice, made basic with 35% aqueous sodium hydroxide and extracted with ether. The ethereal extracts were evaporated to dryness and the residual oil heated under reflux 3 hours in 125 ml. of 12N hydrochloric acid. The resulting mixture was diluted with 300 ml. of water and washed with a mixture of ether and benzene. The aqueous layer was made basic with 35% aqueous sodium hydroxide and extracted with a mixture of ether and benzene. The organic layer was then extracted with 1N hydrochloric acid, the acidic aqueous layer made basic with 35% aqueous sodium hydroxide and extracted with an etherbenzene mixture. The extracts were dried over anhydrous sodium sulfate and evaporated to dryness in vacuo affording 12.2 g of 4-(4-methoxyphenyl)-1,1-dimethylbutylamine as a straw-colored oil.

1. additionTo a stirred mixture of 52.5 g
2. temperatureThe temperature was maintained at 60°-65° C. throughout the addition
3. waitwas continued at 50°-55° C. an additional hour
4. additionafter the addition
5. additionThe reaction mixture was then poured into 850 ml
6. extractionextracted with ether
7. customThe ethereal extracts were evaporated to dryness
8. temperaturethe residual oil heated
9. temperatureunder reflux 3 hours in 125 ml
10. additionThe resulting mixture was diluted with 300 ml
11. washof water and washed with a mixture of ether and benzene
12. extractionextracted with a mixture of ether and benzene
13. extractionThe organic layer was then extracted with 1N hydrochloric acid
14. extractionextracted with an etherbenzene mixture
15. dry with materialThe extracts were dried over anhydrous sodium sulfate
16. customevaporated to dryness in vacuo

ORD record

ord-003bd0442bf543b1879dc31cffe84ab1

Source dataset

uspto-grants-1987_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04695589