Hydrochloric Acid → 2-Chloro-3-(2-chlorophenyl)propanal
Reaction equation
N([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1N.[CH:13]([CH:15]=[CH2:16])=[O:14].[O-2].[Ca+2].[ClH:19]>O.CC(C)=O>[Cl:19][CH:15]([CH2:16][C:7]1[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=1[Cl:5])[CH:13]=[O:14]Participants
Procedure
A solution of sodium nitrite (15 g, 0.22 mol) in water (40 mL) was slowly added to a solution of 2-chloroaniline (25.5 g, 0.200 mol) in hydrochloric acid (20% aqueous solution, 100 mL) at 0 to 5° C. The mixture was stirred for ten minutes and then poured into a cooled (0° C.) solution of acrolein (30. g, 0.56 mol) in acetone (200 mL) containing calcium oxide (4.0 g, 72 mmol), followed by a solution of cuprous chloride (2.0 g, 20 mmol) in acetone (20 mL) containing hydrochloric acid (20% aqueous solution, 4 mL). The mixture was stirred for 3 hours at room temperature, and then extracted three times with dichloromethane (150 mL). The combined organic layers were washed with a solution of saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and evaporated to dryness to give a black viscous oil that was used directly in the next procedure.
Workup
- additionpoured into
- stirringThe mixture was stirred for 3 hours at room temperature
- extractionextracted three times with dichloromethane (150 mL)
- washThe combined organic layers were washed with a solution of saturated aqueous sodium chloride
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated to dryness
- customto give a black viscous oil that
Sources & evidence
- ORD record
- ord-b6e5a05e1c1c4e7ebe97269e50fa23c3
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853415B2
Reaction notes
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