Thionyl Chloride → Methyl 1-chloroindan-4-carboxylate

HRID 1763422

Reaktionsgleichung

Reaktionsgleichung von HRID 1763422
O[CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH2:4][CH2:3]1.S(Cl)([Cl:17])=O>C(Cl)(Cl)Cl>[Cl:17][CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH2:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 20310103Methyl 1-hydroxyindan-4-carboxylate

Produkt 1

HCID 20310089Methyl 1-chloroindan-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In 6 ml. of chloroform is dissolved 5.7 g. of methyl 1-hydroxyindan-4-carboxylate and, under cooling with ice, the solution is stirred. Then, 3 ml. of thionyl chloride is added dropwise and, after the dropwise addition has been completed, the mixture is further stirred under cooling with ice for one hour. Then, the solvent and the excess thionyl chloride are distilled off under reduced pressure. The residue obtained is purified by column chromatography on silica gel (500 g. silica gel; eluant: chloroform). The procedure gives methyl 1-chloroindan-4-carboxylate as an oily product.

Aufarbeitung

  1. additionafter the dropwise addition
  2. stirringthe mixture is further stirred
  3. temperatureunder cooling with ice for one hour
  4. distillationThen, the solvent and the excess thionyl chloride are distilled off under reduced pressure
  5. customThe residue obtained
  6. customis purified by column chromatography on silica gel (500 g. silica gel; eluant: chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-5c52c6d286014d4bb5165b68d9ff3572
Quelldatensatz
uspto-grants-1978_09
Patentnummer
US04111997

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