Hydrochloric Acid → 1-Ethoxy-3-(2-nitroethyl)benzene

Participants

Reaction Conditions

Reaction Steps

A mixture of nitromethane (0.36 mL, 6.7 mmol) and 3-ethoxy-benzaldehyde (1 g, 6.7 mmol) in methanol (1.4 mL) was cooled to −10° C. To this mixture sodium hydroxide (0.28 g in 1 mL water) was added dropwise. The temperature during addition was maintained around 10° C. After 1 hour a yellow precipitate formed and water (5 mL) was added. The resulting solution was added to HCl (4M, 3 mL). The precipitate that formed was filtered off and washed with water. Purification by chromatography on silica, eluting with 1 to 15% ethyl acetate in hexane, gave the subtitled compound as a yellow solid (0.49 g). 1H NMR δ (CDCl3) 1.40-1.48 (3H, t), 4.014.13 (2H, q), 6.97-7.06 (2H, m), 7.09-7.15 (1H, d), 7.30-7.40 (1H, t), 7.53-7.62 (1H, d), 7.91-8.00 (1H, d).

Provenance & Evidence