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Hydrochloric Acid → Methyl 4-chlorocyclohexanecarboxylate

HRID 414647
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 414647
[Cl-].[Al+3].[Cl-].[Cl-].C(OC)(=O)C=C.C=CC(Cl)=C.Cl.[Cl:17][C:18]1[CH2:23][CH2:22][CH:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:20][CH:19]=1.ClC1CC(C(OC)=O)CCC=1>C(Cl)Cl>[Cl:17][CH:18]1[CH2:19][CH2:20][CH:21]([C:24]([O:26][CH3:27])=[O:25])[CH2:22][CH2:23]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 7294Methyl Acrylate2×HCID 31369ChloropreneHCID 6451240Aluminum(III) ChlorideHCID 14365658Methyl 4-chlorocyclohex-3-ene-1-carboxylateHCID 143656591-Chloro-5-carbomethoxy cyclohexene

Produkt 1

HCID 21281591
Methyl 4-chlorocyclohexanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

A mixture of 200 parts of anhydrous aluminum chloride in 2000 parts of methylene chloride was maintained under an atmosphere of nitroge while 129 parts of methyl acrylate was added over a period of about 0.5 hours. With the addition of the methyl acrylate, the temperature of the mixture rose exothermically to about 34° C. The mixture was cooled to about 22° C. and 132.8 parts of freshly prepared chloroprene was added slowly, with stirring over a period of about 1.5 hours. During the addition, the temperature rose slowly to reflux condition (about 40° C.). The reaction mixture was then maintained under a nitrogen atmosphere, with stirring, for about 16 hours at ambient conditions. The crude reaction product was then treated with 10% HCl, and washed with methylene chloride and distilled to yield an essentially pure mixture of 1-chloro-4-carbomethoxy cyclohexene (92%) and its isomer 1-chloro-5-carbomethoxy cyclohexene (8%).

Aufarbeitung

  1. additionwas added over a period of about 0.5 hours
  2. customrose exothermically to about 34° C
  3. additionDuring the addition
  4. temperatureto reflux condition (about 40° C.)
  5. temperatureThe reaction mixture was then maintained under a nitrogen atmosphere
  6. stirringwith stirring, for about 16 hours at ambient conditions
  7. customThe crude reaction product
  8. washwashed with methylene chloride
  9. distillationdistilled
  10. customto yield

Quellen und Nachweise

ORD-Eintrag
ord-0a3b4868c83541a398d89ec083c5ebff
Quelldatensatz
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04792618

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