Benzyl Bromide → ((3-Chloropropoxy)methyl)benzene

HRID 1252565

Reaktionsgleichung

Reaktionsgleichung von HRID 1252565
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].[CH2:6](Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CC(C)([O-])C.[K+]>C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 123133-Chloro-1-propanolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 221505((3-Chloropropoxy)methyl)benzeneAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a 2 l flask, a mixture of 3-chloropropanol (56.7 g), benzyl bromide (102.6 g) and dry THF (600 ml) is stirred and cooled with ice/salt mixture. Potassium tert-butoxide (70 g) is added in portions (5-10 g), maintaining the internal temperature at about 0° C. After the mixture is stirred for 3 more hours at room temperature, the solvent is evaporated. Addition of 1N HCl (1 l), extraction with ether (1 l), and evaporation of solvent gives crude material (113.6 g), which is distilled under vacuum to give 1-chloro-3-benzyloxypropane (108.4 g) b.p.0.01 60°-80° C.

Aufarbeitung

  1. temperaturecooled with ice/salt mixture
  2. stirringAfter the mixture is stirred for 3 more hours at room temperature
  3. customthe solvent is evaporated
  4. additionAddition of 1N HCl (1 l), extraction
  5. customwith ether (1 l), and evaporation of solvent
  6. customgives crude material (113.6 g), which
  7. distillationis distilled under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b483449bc0fd4f7599dd80dfb18cf900
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743691

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