3-Methoxybenzaldehyde → 28446-69-7

Participants

Reaction Steps

Diethylcyanomethyl phosphonate (28.6 mL, 176 mmol) was added to a suspension of NaH (7.0 g, 176 mmol, washed with hexanes to remove oil) in 450 mL of THF at RT and the resulting mixture was stirred at RT for 30 min. A solution of m-anisaldehyde (20.0 g, 140 mmol) in 50 mL of THF was added and the resulting mixture was stirred at RT overnight, resulting in the formation of a thick brown oil at the bottom of the mixture. The crude reaction mixture was concentrated in vacuo and the residue was partitioned between saturated aqueous NaHCO3 solution and methylene chloride. The organic phase was separated and the aqueous phase was extracted with methylene chloride. The combined organic phases were then dried over MgSO4, filtered, and concentrated in vacuo to provide 27.6 g of a brown oil (99% crude yield) which was carried on without further purification. 1H NMR (CDCl3) δ 7.30-7.40 (m, 2H), 6.92-7.05 (m, 3H), 5.86 (d, J=24 Hz, 1H), 3.85 (s, 3H).

Provenance & Evidence