Benzoate → Benzoic Acid

Participants

Reaction Steps

First, 1,3,4,5,6-pentamethyl-Dewar benzene-2-carboxylic acid was synthesized. Ethyl 1,3,4,5,6-pentamethyl Dewar benzoate (5.0 g) was combined with 3.80 g of potassium hydroxide in 50 mL methanol. This solution was stirred at gentle reflux for 16 hours. All methanol was then removed by rotary evaporation, and the resulting residue was dissolved in 75 mL water. To this solution was added 10% HCl (aq) dropwise until the pH of the solution was acidic. The resulting white precipitate was collected by vacuum filtration and dried in a vacuum desiccator overnight to yield 3.70 g of dry white solid (85% yield). The product was analyzed by 1H NMR (CDCl3) δ 2.04 (s, 3H); 1.62 (m, 3H); 1.58 (m, 3H); 1.24 (s, 3H); 1.16 (s, 3H).

Provenance & Evidence