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 (33 ml) was dissolved in 40 ml dichloromethane and added dropwise to the dimethylformamide/dichloro-methane solution at a rate sufficient to maintain the temperature below 25° C. Cyclohexanone (9 g) was added and the mixture heated to reflux for 5 hours. After cooling to room temperature, the reaction mixture was poured into 200 ml of ice and allowed to sit overnight. The quenched mixture was filtered to collect 9.62 g yellow crystals, mp 128° C., λmax (methanol)=328 nm (ε=15,000).

Provenance & Evidence