Phosphorus oxychloride → HCID 19702707, compound
Reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:9]([CH3:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH:17]=[CH2:18])[CH:7]=[CH2:8].[C:20]([O-])(=[O:22])C.[Na+]>CN(C=O)C>[CH2:16]([C:11]1[CH:12]=[C:13]([CH:14]=[CH:15][C:10]=1[N:9]([CH2:6][CH:7]=[CH2:8])[CH3:19])[CH:20]=[O:22])[CH:17]=[CH2:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To dry DMF (25 ml) is added phosphorous oxychloride (15.4 g, 0.10 mol) at 0°-5° C. with mechanical stirring over 0.5 hours. N,2-Diallyl-N-methylaniline (18.7 g, 0.10 mol) in DMF (10 ml) is added in a slow stream with stirring. The mixture is heated to 100° C. with stirring for two hours. The mixture is cooled, poured into ice water (200 ml) and neutralized by slow addition of saturated sodium acetate (150 ml) with stirring. The mixture is extracted with ether two times. The extracts are washed with aqueous saturated sodium bicarbonate (50 ml), water, and then brine solution, dried over potassium carbonate, and concentrated to a solid. The solid is recrystallized from hexane-ethyl acetate to provide pure 3-allyl-4-(N-allyl-N-methylamino)benzaldehyde.
Workup
- stirringwith stirring
- stirringwith stirring for two hours
- temperatureThe mixture is cooled
- stirringwith stirring
- extractionThe mixture is extracted with ether two times
- washThe extracts are washed with aqueous saturated sodium bicarbonate (50 ml), water
- dry with materialbrine solution, dried over potassium carbonate
- concentrationconcentrated to a solid
- customThe solid is recrystallized from hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-cec49ad49bdf476598418c9599687971
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05663308
Reaction notes
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