Isopropyl iodide → 2-Isopropoxy-3-methylbenzaldehyde

Participants

Reaction Steps

Stir a mixture of 3-methylsalicylaldehyde (100 g, 0.73 mol), isopropyl iodide (187 g, 1.1 mol) and K2CO3 (141 g, 1.0 mol) in DMF (400 mL) for 20 hr at room temperature. TLC shows partial reaction; thus, add more isopropyl iodide (43 g, 0.25 mol) and heat the reaction to 45° C. with stirring for an additional 10 hr. Dilute the reaction mixture with H2O (1 L) and extract the resulting mixture with EtOAc. Wash the organic layer with 0.25 M. aqueous NaOH and then with H2O. Dry over MgSO4 and evaporate the solvent to give 3-methyl-2-isopropoxybenzaldehyde, 122 g (94%); 1H-NMR (CDCl3) δ 7.7-7.1 (m, 3H), 4.2 (m, 1H), 2.3 (s, 3H), 1.4 (d. 6H).

Provenance & Evidence