Reaktion #516575

Reaktionsgleichung

3-chloro-4-hydroxybenzoic acid

sodium hydroxide

Propargyl bromide

→

Propargyl 3-Chloro-4-Hydroxybenzoate

Ausbeute 64.3%

Lösungsmittel

isopropyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe solution was heated
2. 2
   Temperaturto reflux for 6 hours
3. 3
   TemperaturThe solution was then cooled
4. 4
   Sonstigethe isopropyl alcohol was removed under vacuum
5. 5
   Waschenwashed with water (200 ml), saturated sodium bicarbonate, saline
6. 6
   Trocknendried over magnesium sulfate
7. 7
   SonstigeRemoval of the solvent
8. 8
   Sonstigeyielded crude product, which
9. 9
   Sonstigewas recrystallized, from CCI4
10. 10
    Sonstigeto give the pure product

Vorschrift

Using the above procedure, 3-chloro-4-hydroxybenzoic acid (0.0826 mole) and sodium hydroxide (0.0826 mole) were dissolved in 50% isopropyl alcohol (200 ml). Propargyl bromide (0.0826 mole) was added and the solution was heated to reflux for 6 hours. The solution was then cooled and the isopropyl alcohol was removed under vacuum. The residue was taken up in methylene chloride (200 ml), washed with water (200 ml), saturated sodium bicarbonate, saline and dried over magnesium sulfate. Removal of the solvent yielded crude product, which was recrystallized, from CCI4 to give the pure product. (64.3% yield) m.p. 144-145° C.

Quelle