Acetone → HCID 20525453, compound

Temperature

90 °C

To the autoclave described in paragraph (b) was charged 4.95 grams (0.03 mole) of the 3-(isopropoxymethyl)aniline prepared in paragraph (b) of this Example and 0.5 gram of 5 percent platinum on carbon hydrogenation catalyst in 230 milliliters of anhydrous acetone. The autoclave was then sealed, the stirrer was turned on, and the temperature was brought up to and maintained at about 90° C. The autoclave was charged with hydrogen gas to a pressure of 100 psi (the valve to the hydrogen cylinder being left open). After 25 hours the autoclave was cooled, broken open, and the contents removed and filtered. The filtrate was concentrated on a rotary evaporator at 55° C., leaving a brown liquid. NMR analysis indicated the brown liquid to be impure. Consequently, the brown liquid was purified by distillation at a pressure of 1.5 millimeters of mercury. A first cut (1.56 grams) was collected at 90° C. to 117° C., which also proved to be quite impure. A second substantially purer cut (1.15 grams) was collected at 118° C. to 122° C., which later was identified by NMR spectroscopy as N-isopropyl 3-(isoproxymethyl)aniline.

1. customThe autoclave was then sealed
2. waitcylinder being left open)
3. temperatureAfter 25 hours the autoclave was cooled
4. customthe contents removed
5. filtrationfiltered
6. concentrationThe filtrate was concentrated on a rotary evaporator at 55° C.
7. customleaving a brown liquid
8. distillationConsequently, the brown liquid was purified by distillation at a pressure of 1.5 millimeters of mercury
9. customA first cut (1.56 grams) was collected at 90° C. to 117° C.
10. customA second substantially purer cut (1.15 grams) was collected at 118° C. to 122° C.

ORD record

ord-3496a57159d1486e9b6dcd3ee8a7ecf5

Source dataset

uspto-grants-1982_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04348223