Reaktion #2304292

Reaktionsgleichung

ethyl 3-(4-hydroxyphenyl)propionate

potassium hydroxide

ethanol

3-[(tosyloxy)methyl]-3-ethyloxetane

→

[4-(3-ethyloxetan-3-ylmethoxy)phenyl]propionic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis was cooled to 40° C.
2. 2
   TemperaturThen, this was refluxed for 3 hours
3. 3
   SonstigeEthanol was evaporated away
4. 4
   workup.ADDITIONwater and toluene were added to it for liquid-liquid separation
5. 5
   WaschenThe toluene layer was washed with 3% hydrochloric acid, saturated sodium hydrogencarbonate and water
6. 6
   Sonstigetoluene was evaporated away
7. 7
   workup.ADDITIONTo the resulting residue, added
8. 8
   Temperaturthis was refluxed for 2 hours
9. 9
   SonstigeEthanol was evaporated away
10. 10
    workup.ADDITIONthe resulting residue was poured into 500 ml of 5% hydrochloric acid
11. 11
    Sonstigea crystal was thus formed
12. 12
    FiltrationThe crystal taken out through filtration
13. 13
    Sonstigewas recrystallized from a mixed solvent of ethanol and water

Vorschrift

17.4 g of ethyl 3-(4-hydroxyphenyl)propionate and 6.1 g of potassium hydroxide were added to 150 ml of ethanol, and stirred at 60° C. for 1 hour. This was cooled to 40° C., and 30 g of 3-[(tosyloxy)methyl]-3-ethyloxetane was dropwise added to it. Then, this was refluxed for 3 hours. Ethanol was evaporated away, and water and toluene were added to it for liquid-liquid separation. The toluene layer was washed with 3% hydrochloric acid, saturated sodium hydrogencarbonate and water, and then toluene was evaporated away. To the resulting residue, added were 20 g of sodium hydroxide, 100 ml of ethanol and 50 ml of water, and this was refluxed for 2 hours. Ethanol was evaporated away, and the resulting residue was poured into 500 ml of 5% hydrochloric acid, and a crystal was thus formed. The crystal taken out through filtration was recrystallized from a mixed solvent of ethanol and water, and 5 g of [4-(3-ethyloxetan-3-ylmethoxy)phenyl]propionic acid (OX7) was obtained. Its melting point was 85° C.

Quelle