1-Chloro-2-methoxy-4-methylbenzene → 4-Chloro-3-methoxybenzaldehyde

Participants

Reaction Steps

Ceric ammonium nitrate (43.3 g, 79.0 mmol, 4.00 equiv) was dissolved in 1:1 HOAc/H2O (200 mL). This solution was added dropwise over one hour to a stirred solution of the product from Step 1 (3.09 g, 19.7 mmol, 1.00 equiv) in 1:1 HOAc/H2O (100 mL) at 100° C. After the addition was complete, the reaction was stirred for an additional 15 minutes. The reaction was cooled, diluted with H2O and extracted twice with Et2O. The combined organic extracts were washed three times with H2O, three times with satd. NaHCO3, and once with brine. The organic phase was dried over MgSO4 and concentrated en vacuo to afford the title compound (3.00 g, 89%) as an amber oil. 1H NMR (400 MHz, CDCL3) 9.97 (s, 1H), 7.57 (d, 1H), 7.46 (s, 1H), 7.43 (d, 1H), 4.00 (s, 3H).

Provenance & Evidence