Hydrochloric Acid → alpha,4-Dichloro-2-(benzoyl)benzenepropanenitrile
Reaction equation
C(ON=O)(C)(C)C.[C:8](#[N:11])[CH:9]=[CH2:10].Cl[C:13]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:14]=1[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:16].CCOCC.[ClH:33]>C(#N)C.O>[Cl:33][CH:9]([CH2:10][C:13]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:14]=1[C:15](=[O:16])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:8]#[N:11]Participants
Procedure
A solution of 92.7 g (0.4 mol) of 2-amino-5-chlorobenzephenone in 250 ml of acetonitrile was added to a mixture of 70 g (0.52 mol) of cupric chloride, 65 g (0.63 mole) of t-butylnitrite, 500 ml of acrylonitrile and 500 ml of acetonitrile. When the addition was complete, stirring at room temperature was continued for 2 hours. The mixture was diluted with 80 ml of 6 N hydrochloric acid and 1500 ml of water, extracted with ether and dried over anhydrous sodium sulfate. The ether solution was concentrated at reduced pressure to give a brown oil, which contained the end product and 2,5-dichlorobenzophenone. Trituration of the oil with a mixture of ether and petroleum ether gave the end product as a tan solid. Recrystallization of a small portion of the end product from a mixture of ether and petroleum ether gave pale yellow needles, mp 69°-71° C.
Workup
- additionWhen the addition
- extractionextracted with ether
- dry with materialdried over anhydrous sodium sulfate
- concentrationThe ether solution was concentrated at reduced pressure
- customto give a brown oil, which
Sources & evidence
- ORD record
- ord-ff85182617fc4fb1b3da3142608522e9
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04436662
Reaction notes
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