Hydrochloric Acid → 3-Cyano-4-methoxybenzoic acid

To a stirred solution of methyl 3-cyano-4-methoxybenzoate (1.1 g, 5.70 mmol) in a mixture of THF (70 mL), MeOH (70 mL) and water (5 mL) was added LiOH (0.97 g, 23.01 mmol) at RT and the reaction mixture was then stirred at RT for 1 h. The reaction mixture was acidified to pH ˜2 with 2 N HCl and the aqueous layer was extracted with DCM (3×100 mL). The combined organic extracts were washed with water (50 mL) and brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to afford 3-cyano-4-methoxybenzoic acid (1.0 g, 100%) as a solid.

1. extractionthe aqueous layer was extracted with DCM (3×100 mL)
2. washThe combined organic extracts were washed with water (50 mL) and brine (50 mL)
3. dry with materialdried over anhydrous Na2SO4
4. filtrationfiltered
5. customevaporated under reduced pressure

ORD record

ord-90cbbc102db3407ca3026f0cad53c7bf

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071595B2