Dimethylformamide → 2-Chloro-3-(hydroxymethylidene)cyclohex-1-ene-1-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Dimethylformamide (40 mL) and 40 mL dichloromethane were mixed and cooled to 5° C. Phosphorous oxychloride (37 mL) was dissolved in 40 mL dichloromethane and added dropwise to the dimethylformamide/dichloromethane solution at rate to maintain the temperature below 25° C. Cyclohexanone (10 g, 0.102 mol) was added and the mixture heated at reflux for 3 hours. After cooling to room temperature, the reaction mixture was poured into 200 mL of ice and allowed to sit overnight. The quenched reaction mixture was filtered to collect 3.59 g solid, mp 127° C., λmax =325 nm (ε=14,000).

Provenance & Evidence