Reaktion #322870

Reaktionsgleichung

4-hydroxyphenylacetic acid

1-tetradecylbromide

sodium hydroxide

→

desired title compound

Ausbeute 38.4%

(4-Tetradecyloxyphenyl)acetic acid

Ausbeute 38.4%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for about 24 hours
2. 2
   Sonstigethe aqueous layer decanted
3. 3
   Waschenthe solid washed with water
4. 4
   TemperaturThe solid was refluxed for about 2 hours
5. 5
   workup.STIRRINGwith stirring in about 500 ml of ethanol containing about 40 g of sodium hydroxide and about 40 ml of water
6. 6
   SonstigeThe solvents were removed
7. 7
   Temperaturthe residue heated at about 0.1 mm and about 200°-210° C. in a Kugelrohr
8. 8
   workup.STIRRINGThe residue was stirred with dilute hydrochloric acid and ethyl acetate on a steam bath until solution
9. 9
   WaschenThe warm solution was washed with brine
10. 10
    Sonstigethe solvent was removed
11. 11
    Sonstigethe residue recrystallized sequentially from methanol and hexane

Vorschrift

A mixture of about 75 g of 4-hydroxyphenylacetic acid, about 273.38 g of 1-tetradecylbromide, about 46.33 g of sodium hydroxide, about 5.0 g of trioctadecyl methylamine chloride and about 500 ml of water was refluxed for about 24 hours with stirring, cooled to room temperature, the aqueous layer decanted and the solid washed with water. The solid was refluxed for about 2 hours with stirring in about 500 ml of ethanol containing about 40 g of sodium hydroxide and about 40 ml of water. The solvents were removed and the residue heated at about 0.1 mm and about 200°-210° C. in a Kugelrohr. The residue was stirred with dilute hydrochloric acid and ethyl acetate on a steam bath until solution was complete. The warm solution was washed with brine, then the solvent was removed and the residue recrystallized sequentially from methanol and hexane, giving about 66 g of the desired title compound as a white solid, mp 86°-87° C.

Quelle