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 (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).
Workup
- temperatureto maintain the temperature below 25° C
- temperaturethe mixture heated
- temperatureat reflux for 3 hours
- temperatureAfter cooling to room temperature
- customThe quenched reaction mixture
- filtrationwas filtered
- customto collect 3.59 g solid, mp 127° C., λmax =325 nm (ε=14,000)
Sources & evidence
- ORD record
- ord-dabc4f70d2684e1da24d3c3fe999d9c9
- Source dataset
- uspto-grants-1992_11
- Patent number
- US05164291
Reaction notes
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