Imidazole → 3-Hydroxybenzoic Acid

Into a 250 mL round bottom flask was added 50 mL of dry dimethyl formamide. Ffifteen parts of the hydroxy benzoate (27) and seventeen parts of tert-butyldimethyl silyl chloride were added to the reaction flask with stirring. Seventeen parts of Imidazole was added in portions and stirring was continued for 10 hours. The reaction mixture was extracted with (3×300 mL) of hexane and the hexane layer was washed twice with 250 mL of water. The organic layer was dried on anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give an oil, yield 26 parts. This material was pure enough for the next step of the reaction. The material was prepared according to the following equation:

1. stirringstirring
2. extractionThe reaction mixture was extracted with (3×300 mL) of hexane
3. washthe hexane layer was washed twice with 250 mL of water
4. dry with materialThe organic layer was dried on anhydrous sodium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customto give an oil

ORD record

ord-8eb9d7918bb946728c57917cc7d57be1

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07416898B2