Iodoethane → 224789-17-7

To a solution of 2-hydroxy-4-methoxy-benzonitrile (9.637 g, 64.61 mmol) in ethanol (50 mL) were added potassium carbonate (17.88 g, 129.2 mmol) and iodoethane (15.7 mL, 193.8 mmol). The reaction mixture was heated at gentle reflux for 12 h. The solvent was removed to afford a yellow-brown paste. It was then taken in diethyl ether (50 mL) and water (20 mL). The layers were separated and the aqueous layer was extracted with diethyl ether (2×150 mL). The combined organic extracts were washed with water (1×20 mL), brine (1×20 mL), and dried over anhydrous sodium sulfate. The solids were then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel) eluting with 10–15% ethyl acetate in hexanes yielded 2-ethoxy-4-methoxy-benzonitrile as yellow solids (9.487 g, 83%).

1. temperatureThe reaction mixture was heated
2. temperatureat gentle reflux for 12 h
3. customThe solvent was removed
4. customto afford a yellow-brown paste
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with diethyl ether (2×150 mL)
7. washThe combined organic extracts were washed with water (1×20 mL), brine (1×20 mL)
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe solids were then filtered off
10. concentrationthe filtrate was concentrated in vacuo
11. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32–63 μm, 60 Å silica gel)
12. washeluting with 10–15% ethyl acetate in hexanes

ORD record

ord-1e23e67d5b3340189cb71ed7029d0604

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07132421B2