Ethyl cyanoacetate → Ethyl 1-cyano-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate

HRID 894492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894492
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[Cl:9][C:10]([Cl:18])=[CH:11][CH:12](Br)[C:13](Br)([CH3:15])[CH3:14]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O.C1(C)C=CC=CC=1>[C:1]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:12]([CH:11]=[C:10]([Cl:18])[Cl:9])[C:13]1([CH3:15])[CH3:14])#[N:2]

Komponenten

6

Edukt 2

HCID 7764Ethyl cyanoacetateHCID 205742811,1-Dichloro-3,4-dibromo-4-methylpent-1-ene

Produkt 1

HCID 12898169Ethyl 1-cyano-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylateAusbeute 31,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of ethyl cyanoacetate (12.44 parts), 1,1-dichloro-3,4-dibromo-4-methylpent-1-ene (31.1 parts), cupric acetate monohydrate (20 parts), benzyltriethylammonium chloride (4.54 parts) and water (100 parts) is stirred at 95°-100° C. for 6 hours. The mixture is cooled and diluted with water (100 parts and toluene (100 parts by volume), and filtered to remove insoluble material. The filter-cake is washed twice with toluene (20 parts by volume) and twice with water (50 parts). The filtrates and washes are separated and the toluene layer is washed with concentrated hydrochloric acid (50 parts by volume) diluted with water (50 parts) and then four times with water (50 parts). The toluene is removed by evaporation under reduced pressure to give ethyl 1-cyano-3-(2',2'-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate, strength 53.3% and cis-cyano:trans-cyano ratio 69.2:30.8 in 31.2% yield.

Aufarbeitung

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. customto remove insoluble material
  4. washThe filter-cake is washed twice with toluene (20 parts by volume) and twice with water (50 parts)
  5. customThe filtrates and washes are separated
  6. washthe toluene layer is washed with concentrated hydrochloric acid (50 parts by volume)
  7. additiondiluted with water (50 parts)
  8. customThe toluene is removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f31098909f214e169ccaf6b8058c82fd
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04284582

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