Hydrochloric Acid → (E)-3-(3-nitrophenyl)prop-2-en-1-ol

Temperature

0 °C

To a solution of ethyl (E)-3-(3-nitrophenyl)-2-propenoate (8.04 g, 36 mmol) in dichloromethane at 0° C. under nitrogen was added dropwise over 5 minutes diisobutylaluminium hydride (1.0 M solution in dichloromethane, 80 ml, 80 mmol). The mixture was stirred at 0° C. for 10 minutes, then allowed to warm to room temperature over 30 minutes. Hydrochloric acid (1N, 500 ml) was added, the layers were separated and the aqueous layer was extracted with dichloromethane (2×250 ml). The organic layers were combined, washed with brine (2×100 ml), filtered and concentrated in vacuo to give the title compound as a red oil.

1. temperatureto warm to room temperature over 30 minutes
2. customthe layers were separated
3. extractionthe aqueous layer was extracted with dichloromethane (2×250 ml)
4. washwashed with brine (2×100 ml)
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-79eccb75da7149759fd8d664643490ce

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049444B2