Hydrochloric Acid → Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

HRID 557846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557846
[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].Cl>C(=S)=S>[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 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12861006Methyl 1-phenylcyclopropane-1-carboxylate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6348Carbon DisulfideLösungsmittel

Versuchsvorschrift

Aluminium trichloride (7.9 g, 60.0 mmol) was added in portions to a mixture of methyl 1-phenylcyclopropanecarboxylate (3.5 g, 20.0 mmol) and chloroacetyl chloride (2.0 mL, 26.0 mmol) in carbon disulfide (40.0 mL) at 15-25° C. The reaction mixture was stirred for 2 hours at room temperature. Then the mixture was poured into concentrated HCl (10.0 mL) in ice (100 g). The resulting mixture was extracted with diethyl ether several times. The combined organic phase was washed with brine, then dried and concentrated. The crude product was purified by CombiFlash using hexane/ethyl acetate.

Aufarbeitung

  1. extractionThe resulting mixture was extracted with diethyl ether several times
  2. washThe combined organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was purified by CombiFlash

Quellen und Nachweise

ORD-Eintrag
ord-6dec0c7e6ece419283a5520acc2829d9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058288B2

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