반응 #322870

반응 방정식

4-hydroxyphenylacetic acid

1-tetradecylbromide

sodium hydroxide

→

desired title compound

수율 38.4%

(4-Tetradecyloxyphenyl)acetic acid

수율 38.4%

용매

water

반응 조건

후처리

1. 1
   온도was refluxed for about 24 hours
2. 2
   기타the aqueous layer decanted
3. 3
   세척the solid washed with water
4. 4
   온도The 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
   기타The solvents were removed
7. 7
   온도the 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
   세척The warm solution was washed with brine
10. 10
    기타the solvent was removed
11. 11
    기타the residue recrystallized sequentially from methanol and hexane

실험 절차

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.

출처