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

HRID 894488

Reaktionsgleichung

Reaktionsgleichung von HRID 894488
[Cl:1][C:2]([Cl:8])=[CH:3][CH:4]=[C:5]([CH3:7])[CH3:6].Br[CH:10]([C:16]#[N:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[Ca+2].[Ca].[Cl-].[Na+].Cl>[Cu].C(OCCCC)(=O)C.O>[CH2:14]([O:13][C:11]([C:10]1([C:16]#[N:17])[CH:4]([CH:3]=[C:2]([Cl:8])[Cl:1])[C:5]1([CH3:7])[CH3:6])=[O:12])[CH3:15]

Komponenten

10

Edukt 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 10112Calcium CarbonateHCID 14469Ethyl 2-bromo-2-cyanoacetateHCID 1087461,3-Pentadiene, 1,1-dichloro-4-methyl-HCID 5460341Calcium

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 962WaterLösungsmittel2×HCID 31272Butyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1,1-dichloro-4-methylpenta-1,3-diene (30.2 parts), ethyl bromocyanoacetate (38.4 parts), calcium carbonate (20 parts), copper catalyst, phase transfer catalyst and calcium or sodium chloride (each as indicated in the table below) and water (100 parts) is heated at 80° C. and held at 80° C. for 6 hours. The reaction mixture is cooled and stirred with water (100 parts), butyl acetate (100 parts by volume) and concentrated hydrochloric acid (100 parts by volume). The mixture is filtered and the residue is washed with butyl acetate (2×20 parts by volume). The filtrate and washes are combined and the butyl acetate layer is separated and washed with water (4×50 parts). The crude ethyl-1-cyano-3-(2',2'-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate is isolated by removal of the butyl acetate under reduced pressure.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe mixture is filtered
  3. washthe residue is washed with butyl acetate (2×20 parts by volume)
  4. customthe butyl acetate layer is separated
  5. washwashed with water (4×50 parts)

Quellen und Nachweise

ORD-Eintrag
ord-db4f54f5210949e58fe9a53847bdc973
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04284582

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