Carbon Disulfide → Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

HRID 504338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 504338
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]1([C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Cl:18][CH2:19][C:20](Cl)=[O:21].C(=S)=S>Cl>[Cl:18][CH2:19][C:20]([C:8]1[CH:9]=[CH:10][C:5]([C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)=[CH:6][CH:7]=1)=[O:21]

Komponenten

6

Edukt 4

HCID 6348Carbon DisulfideHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Produkt 1

HCID 86602275Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

Aluminum trichloride (7.9 g, 0.060 mol) was added in portions to a mixture of methyl 1-phenylcyclopropanecarboxylate (3.5 g, 0.020 mol) and chloroacetyl chloride (2.0 mL, 0.026 mol) in carbon disulfide (40 mL, 0.7 mol) at 15-25° C. and then the reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into conc. HCl (10 mL) in ice (100 g) and then extracted with ether. The ether extract was washed with brine, dried and concentrated. The product was purified by CombiFlash using hexane/EtOAc (max.EA 20%). The final product was analyzed by 1H NMR, which showed that the product was a mixture of para and meta substituted isomers with a ratio of 3:2.

Aufarbeitung

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe product was purified by CombiFlash
  7. additiona mixture of para and meta

Quellen und Nachweise

ORD-Eintrag
ord-7236739dc02b441a995485cfde207d0f
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07776874B2

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