2-Methoxy-3-methylbenzaldehyde

824-42-0

74-88-4

67639-61-6

1. 2-Hydroxy-3-methylbenzaldehyde (80 g, 0.588 mol) was dissolved in 350 mL of N,N-dimethylformamide (DMF) and preheated at 50°C. The solution was then dissolved in a mixture of potassium carbonate and potassium iodide. 2. Potassium carbonate (97.4 g, 0.705 mol) was added to the solution, followed by slow dropwise addition of methyl iodide (125 g, 0.881 mol). 3. After stirring the reaction for 1 hour at 50°C, the reaction mixture was cooled to room temperature. 4. 700 mL of water was added to the cooled reaction mixture and the pH was adjusted to 7 with 3N hydrochloric acid. 5. The mixture was extracted twice with 350 mL of ethyl acetate and the organic layers were combined. 6. The combined organic layers were washed with saturated brine and dried with anhydrous sodium sulfate. 7. The solvent was removed under pressure to give 87.9 g (99.9% yield) of 2-methoxy-3-methylbenzaldehyde. The product was confirmed by 1H NMR (DMSO-d6): δ 10.25 (s, 1H), 7.60 (m, 1H), 7.20 (m, 1H), 3.85 (s, 3H), 2.28 (s, 3H).