Dimethylformamide → 2-Chloro-3-(hydroxymethylidene)cyclohex-1-ene-1-carbaldehyde
Reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.CN(C)C=O.Cl[CH2:17][Cl:18].[C:19]1(=[O:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCl>[Cl:18][C:17]1[C:20](=[CH:19][OH:25])[CH2:21][CH2:22][CH2:23][C:24]=1[CH:3]=[O:4]Participants
6
Conditions
- Temperature
- 5 °C
Procedure
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).
Workup
- temperatureto maintain the temperature below 25° C
- temperaturethe mixture heated
- temperatureto reflux for 5 hours
- temperatureAfter cooling to room temperature
- filtrationThe quenched mixture was filtered
- customto collect 9.62 g yellow crystals, mp 128° C., λmax (methanol)=328 nm (ε=15,000)
Sources & evidence
- ORD record
- ord-748cc6d8683b4d3188d448e7807b186e
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05932740
Reaction notes
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