Reaktion #981792

Reaktionsgleichung

methyl 5-benzyloxysalicylate

potassium carbonate

α-bromo-γ-butyrolactone

→

α-[(2-carboxy-4-benzyloxyphenyl)oxy]-γ-butyrolactone

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder cooling with ice
2. 2
   Temperaturthe mixture was refluxed for 15 hours
3. 3
   TemperaturAfter cooling
4. 4
   workup.DISTILLATIONthe acetone was distilled off
5. 5
   workup.ADDITION10% methanolic sodium hydroxide was added to the residue for hydrolysis
6. 6
   Extraktionextracted with ethyl acetate
7. 7
   WaschenThe extract was washed with water
8. 8
   Trocknendried over anhydrous sodium sulfate
9. 9
   workup.DISTILLATIONdistilled
10. 10
    Sonstigeto remove the solvent
11. 11
    workup.DISSOLUTIONThe residue was dissolved in dioxane (300 ml)-benzene (200 ml)
12. 12
    Temperaturthe solution was refluxed in the presence of p-toluenesulfonic acid (30 g), with the resultant water being
13. 13
    workup.DISTILLATIONcontinuously distilled off
14. 14
    workup.DISTILLATIONThe solvent was distilled off
15. 15
    workup.ADDITIONthe residue was diluted with water
16. 16
    Extraktionextracted with ethyl acetate
17. 17
    WaschenThe extract was washed with water
18. 18
    Sonstigedried
19. 19
    Einengenconcentrated
20. 20
    Sonstigeto remove the solvent
21. 21
    SonstigeThe residue was recrystallized from ethyl acetate

Vorschrift

To a mixture of 32 g of methyl 5-benzyloxysalicylate, 17 g of anhydrous potassium carbonate and 500 ml of acetone was added 30.7 g of α-bromo-γ-butyrolactone under cooling with ice and, then, the mixture was refluxed for 15 hours. After cooling, the acetone was distilled off and 10% methanolic sodium hydroxide was added to the residue for hydrolysis. The reaction mixture was made acidic with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was dissolved in dioxane (300 ml)-benzene (200 ml) and the solution was refluxed in the presence of p-toluenesulfonic acid (30 g), with the resultant water being continuously distilled off. The solvent was distilled off and the residue was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated to remove the solvent. The residue was recrystallized from ethyl acetate. By the above procedure there was obtained α-[(2-carboxy-4-benzyloxyphenyl)oxy]-γ-butyrolactone as colorless needles, m.p. 120°-122° C.

Quelle