1-Bromo-3-chloropropane → Ethyl 4-(3-chloropropoxy)benzoate

HRID 268703Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268703
[OH:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.Br[CH2:14][CH2:15][CH2:16][Cl:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:17][CH2:16][CH2:15][CH2:14][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 8434EthylparabenHCID 11430Potassium Carbonate

Produkt 1

HCID 18348522Ethyl 4-(3-chloropropoxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Ethyl 4-hydroxybenzoate (60.0 g), 1-bromo-3-chloropropane (71.37 ml) and potassium carbonate (149.61 g) were heated under reflux in acetone (1445 ml) overnight. The reaction mixture was then allowed to cool to rt, filtered and evaporated. The residue was chromatographed [silica gel; step gradient 0-5% ethyl acetate/hexane]. Fractions containing pure product were combined and evaporated to give the subtitled compound as a clear oil (70.0 g). MS electrospray (+ion) 243 (MH+). 1H NMR δ (CDCl3): 8.00 (2H, d, J=8.8 Hz), 6.92 (2H, d, J=8.8 Hz), 4.36 (2H, q, J=7.1 Hz), 4.18 (2H, t, J=5.8 Hz), 3.74 (2H, t, J=6.2), 2.25 (2H, m), 1.37 (3H, t, J=7.1 Hz).

Aufarbeitung

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was chromatographed [silica gel; step gradient 0-5% ethyl acetate/hexane]
  4. additionFractions containing pure product
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4b1266b4c0a54aa183d5e20eefbdd13a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446103B2

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