Reaction #955936

Reaction equation

Methyl 4-ethyl-2-methoxybenzoate

→

4-ethyl-2-methoxybenzoic acid

Yield 97.0%

Solvents

NaOH

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled to rt
2. 2
   Washwashed with hexanes
3. 3
   OtherThe aqueous layer was then separated
4. 4
   OtherA white precipitate was collected
5. 5
   Washwashed with water
6. 6
   Otherdried

Procedure

Methyl 4-ethyl-2-methoxybenzoate (example 18c) (2.01 g, 10.3 mmol) was suspended in 1M aq. NaOH (40 mL) and the mixture was stirred at 60° C. overnight. The reaction mixture was cooled to rt and washed with hexanes. The aqueous layer was then separated and acidified with 6N HCl to pH 2. A white precipitate was collected washed with water and dried to give 4-ethyl-2-methoxybenzoic acid (1.8 g, 97%) as a white solid. 1H NMR (300 MHz, dMSO): δ 1.16-1.20 (t, 3H), 2.60-2.65 (dd, 2H), 3.80 (s, 3H), 6.82-6.84 (d, 1H), 6.95 (s, 1H), 7.57-7.59 (d, 1H).

Source