3-(propan-2-yloxymethyl)aniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. The autoclave was then sealed cylinder being left open) After 25 hours the autoclave was cooled the contents removed filtered The filtrate was concentrated on a rotary evaporator at 55° C. leaving a brown liquid 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. A second substantially purer cut (1.15 grams) was collected at 118° C. to 122° C.