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

HRID 894495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 894495
[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].[Ca].C(=O)([O-])[O-].[Mg+2].[Cl-].Cl>O.[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.[Cl-].C[N+](CC)(CC)CC.[Cu].C(OCCCC)(=O)C>[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

12

Edukt 6

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 11029Magnesium CarbonateHCID 5460341CalciumHCID 205742811,1-Dichloro-3,4-dibromo-4-methylpent-1-ene

Produkt 1

HCID 12898169Ethyl 1-cyano-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 5974Hexadecyltrimethylammonium BromideKatalysatorHCID 23978CopperKatalysatorHCID 82326Triethylmethylammonium chlorideKatalysatorHCID 962WaterLösungsmittel2×HCID 31272Butyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of ethyl cyanoacetate (24.88 parts), 1,1-dichloro-3,4-dibromo-4-methylpent-1-ene (62.2 parts), calcium or magnesium carbonate and metal chloride is heated in water (100 parts) in the presence of a phase transfer catalyst (either cetyl trimethyl ammonium bromide (CTMAB) or methyl triethyl ammonium chloride (MTEAC)]] and a copper salt as catalyst. The reaction mass is cooled to room temperature, n-butyl acetate (100 parts by volume) water (100 parts) and hydrochloric acid (100 parts by volume) are added and the mixture is stirred for 30 minutes, filtered from extraneous matter and the filtrates separated. The butyl acetate layer is washed with water (4×100 parts) and evaporated under reduced pressure to remove the butyl acetate and yield the crude ethyl 1-cyano-3-(2',2'-dichlorovinyl)-2,2-dimethyl-cyclopropane-1-carboxylate. The yield, strength and composition of the product is given in the following table, together with other details.

Aufarbeitung

  1. filtrationfiltered from extraneous matter
  2. customthe filtrates separated
  3. washThe butyl acetate layer is washed with water (4×100 parts)
  4. customevaporated under reduced pressure
  5. customto remove the butyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-1f98ea6235da407b987a205ab0fdcc38
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04284582

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