Hydrochloric Acid → 3-Carboxybenzaldehyde

A mixture of methyl 3-formylbenzoate (6.15 g, 37.46 mmol) in methanol (61.5 mL) and 2 M sodium hydroxide aqueous solution (37.5 mL, 75 mmol) was stirred at r.t. for 1 h, Thin layer chromatography (Petroleum ether:ethyl acetate=1:1) showed the reaction was complete. The reaction mixture was acidified with 80 mL of 1 M hydrochloric acid aqueous solution to pH=2 and the resulting mixture was concentrated in vacuo. The residue was extracted with ethyl acetate for 3 times and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate. Removal of the solvent in vacuo gave 5.59 g of 3-formylbenzoic acid as a white solid. Yield: 99.5%.

1. concentrationthe resulting mixture was concentrated in vacuo
2. extractionThe residue was extracted with ethyl acetate for 3 times
3. washthe combined organic layers were washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. customRemoval of the solvent in vacuo

ORD record

ord-4e40cab4fd6a4bfe95375b09b353e9c5

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586747B2