1-Bromo-3-chloropropane → 4-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl ester

HRID 1193652

Reaktionsgleichung

Reaktionsgleichung von HRID 1193652
[C:1]([O:13][CH2:14][CH3:15])(=[O:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.Br[CH2:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:13][C:1](=[O:12])[CH2:2][C:3]1[CH:11]=[CH:10][C:8]([O:9][CH2:17][CH2:18][CH2:19][Cl:20])=[C:5]([O:6][CH3:7])[CH:4]=1)[CH3:15]

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 108965Ethyl homovanillate

Produkt 1

HCID 144071784-(3-Chloropropoxy)-3-methoxybenzeneacetic acid ethyl esterAusbeute 65,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 50 g (0.238 mole) of ethyl homovanillate, 75 g (0.476 mole) of 1-bromo-3-chloropropane and 98.7 g (0.71 mole) of anhydrous potassium carbonate in 1 liter of acetone was heated at reflux for 24 hr. The mixture was filtered and the filtrate was concentrated under reduced pressure to give an oil which gradually crystallized to a semi-solid. The solid was recrystallized from ethyl ether-petroleum ether (30°-60° C.) to yield 44.4 g (65%) of white solid, m.p. 36°-38° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customto give an oil which
  6. customgradually crystallized to a semi-solid
  7. customThe solid was recrystallized from ethyl ether-petroleum ether (30°-60° C.)

Quellen und Nachweise

ORD-Eintrag
ord-5fc14b69f2cf4e82b434f8b3c23df8ee
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04810713

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