Dimethylformamide → 2-chloro-4,4-diMethylcyclohex-1-enecarbaldehyde
Reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)([Cl:8])=O.[CH3:11][C:12]1([CH3:19])[CH2:17][CH2:16][CH2:15][C:14](=O)[CH2:13]1>ClCCl>[Cl:8][C:14]1[CH2:13][C:12]([CH3:19])([CH3:11])[CH2:17][CH2:16][C:15]=1[CH:3]=[O:4]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
Into a 250 mL round-bottomed flask was added N,N-dimethylformamide (3.5 mL) in dichloromethane (30 mL). The mixture was cooled to −10° C., and phosphoryl trichloride (4 mL) was added dropwise. The solution was warmed up to room temperature and 3,3-dimethylcyclohexanone (5.5 mL) was added slowly. The mixture was heated to reflux overnight. The reaction mixture was quenched with a 0° C. solution of sodium acetate (25 g in 50 mL water). The aqueous layer was extracted with ether (3×200 mL). The organic layers were combined, dried over Na2SO4, filtered, and dried under vacuum to give the title compound.
Workup
- temperatureThe solution was warmed up to room temperature
- temperatureThe mixture was heated
- temperatureto reflux overnight
- customThe reaction mixture was quenched with a 0° C. solution of sodium acetate (25 g in 50 mL water)
- extractionThe aqueous layer was extracted with ether (3×200 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- customdried under vacuum
Sources & evidence
- ORD record
- ord-869158c1216c45f6a24093be63d55077
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029404B2
Reaction notes
Loading…