Ethyl 2-methyl-2-(4-nitrophenyl)propanoate → 2-Methyl-2-(4-nitrophenyl)propan-1-ol

Temperature

0 °C

In a 250 mL oven-dried flask capped with a rubber septum and placed under a nitrogen atmosphere was charged ethyl 2-methyl-2-(4-nitrophenyl)propanoate (5.0 g, 21 mmol), anhydrous tetrahydrofuran (42 mL) and the flask was cooled to 0° C. To this was added via an addition funnel diisobutylaluminum hydride solution (63 mL, 1M in tetrahydrofuran) and the flask was allowed to warm to ambient temperature and stirred for 16 h. The reaction was quenched with Rochelle's salt, stirred for 30 min and filtered over Celite®. The solution was extracted three times with ethyl acetate and the combined organics were washed once each with Rochelle's salt, water, and brine. The organics were dried over sodium sulfate, filtered and concentrated in vacuo to give 2-methyl-2-(4-nitrophenyl)propan-1-ol (4.1 g, 99%).

1. customIn a 250 mL oven-dried flask
2. customcapped with a rubber septum
3. temperatureto warm to ambient temperature
4. customThe reaction was quenched with Rochelle's salt
5. stirringstirred for 30 min
6. filtrationfiltered over Celite®
7. extractionThe solution was extracted three times with ethyl acetate
8. washthe combined organics were washed once each with Rochelle's salt, water, and brine
9. dry with materialThe organics were dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-d198b532a12e42ae8a087197deeecc3f

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960569B2