Nitroethane → 2-Hydroxy-4-methoxybenzonitrile

A mixture of the 2-hydroxy-4-methoxybenzaldehyde (20 g, 128.8 mmol), sodium acetate (35.05 g, 257.6 mmol) and nitroethane (19 mL, 257.6 mmol) in glacial acetic acid (100 mL) was heated at gentle reflux for 12 h. The reaction mixture was then poured into ˜1000 mL of ice water (1:1 ratio of ice and water). The product was extracted with ethyl acetate (3×200 mL). The organic extracts were washed with sodium bicarbonate solution until the aqueous layer had pH ˜8. The organic layers were then dried over anhydrous magnesium sulfate and concentrated in vacuo to afford 2-hydroxy-4-methoxy-benzonitrile as a yellow oil (16.5 g, 86%). It was used without further purification.

1. temperaturewas heated
2. temperatureat gentle reflux for 12 h
3. extractionThe product was extracted with ethyl acetate (3×200 mL)
4. washThe organic extracts were washed with sodium bicarbonate solution until the aqueous layer
5. dry with materialThe organic layers were then dried over anhydrous magnesium sulfate
6. concentrationconcentrated in vacuo

ORD record

ord-e5a769c3bc2d4c87bb9b20d92c92ebdd

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132421B2