Sodium Cyanide → Methyl 3-cyano-4-hydroxybenzoate

Temperature

105 °C

Methyl-4-hydroxy-3-iodobenzoate (2.00 g, 7.2 mmol) was dissolved into 5 mL of dry DMF. Copper(I) cyanide (0.72 g, 8.0 mmol) and a small crystal of sodium cyanide was added. The mixture was flushed with nitrogen, placed in an oil heating bath (100-110° C.), and stirred overnight. TLC indicated nearly complete reaction. The mixture was cooled and the solids removed by filtration. The solids were extracted with DMF (3 mL). The filtrate and washings were taken up in 100 mL of ethyl acetate, then washed with 3 portions of saturated sodium chloride solution. The solids and aqueous washings were combined, and shaken with a mixture of 50 mL of ethyl acetate and a ferric chloride solution (4 g of hydrated ferric chloride in 7 mL of conc. hydrochloric acid). The ethyl acetate layers were combined, washed with brine containing sodium metabisulfite, dried over sodium sulfate, filtered, and the solvent removed in vacuo. The resulting solids were purified by flash chromatography on silica gel (20% ethyl acetate/hexane) to afford methyl-3-cyano-4-hydroxybenzoate, 0.93g (73%).

1. customThe mixture was flushed with nitrogen
2. customreaction
3. temperatureThe mixture was cooled
4. customthe solids removed by filtration
5. extractionThe solids were extracted with DMF (3 mL)
6. washwashed with 3 portions of saturated sodium chloride solution
7. stirringshaken with a mixture of 50 mL of ethyl acetate
8. washwashed with brine
9. additioncontaining sodium metabisulfite
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. customthe solvent removed in vacuo
13. customThe resulting solids were purified by flash chromatography on silica gel (20% ethyl acetate/hexane)

ORD record

ord-833aa09cbcd540128376668df169f86d

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06613942B1