Reaktionsgleichung
[C-:1]#[N:2].[Na+].O.[O:5]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:20][C:21]([Cl:31])=[CH:22][C@@H:23]1[C@H:25]([C:26](Cl)=[O:27])[C:24]1([CH3:30])[CH3:29]>C(#N)C>[Cl:20][C:21]([Cl:31])=[CH:22][C@@H:23]1[C@H:25]([C:26]([O:16][CH:15]([C:1]#[N:2])[C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([O:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:13]=2)=[O:27])[C:24]1([CH3:30])[CH3:29]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of sodium cyanide (0.74 g, 0.015 mold) in a 1:1 by volume mixture of water and acetonitrile (20 ml) at room temperature was added all at once 3-phenoxybenzaldehyde (1.98 g, 0.01 mole) in the same solvent system (5 ml) followed by a dropwise addition over 10 minutes of cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarbonyl chloride (2.73 g, 0.012 mole). Stirring was continued at room temperature for 2 hours, after which the mixture was extracted thrice with methylene chloride (30 ml each). The combined organic layers were washed once with aqueous 2 N NaOH (25 ml), then thrice with water (25 ml each) to a final wash pH of about 6, dried over Na2SO4, and concentrated to give α-cyano-3-phenoxybenzyl cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (3.76 g, 90% yield).
Aufarbeitung
- extractionafter which the mixture was extracted thrice with methylene chloride (30 ml each)
- washThe combined organic layers were washed once with aqueous 2 N NaOH (25 ml)
- washthrice with water (25 ml each) to a final wash pH of about 6
- dry with materialdried over Na2SO4
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-a856b7c602e944feb3c1cb8bc9a71c96
- Quelldatensatz
- uspto-grants-1981_11
- Patentnummer
- US04299776
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