反応 #2304291

反応方程式

ethyl hydroxycinnamate

potassium hydroxide

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

→

4-(3-ethyloxetan-3-ylmethoxy)cinnamic acid

収率 19.3%

溶媒

ethanol

反応条件

後処理

1. 1
   温度This was cooled to 40° C.
2. 2
   温度Then, this was refluxed for 3 hours
3. 3
   その他Ethanol was evaporated away
4. 4
   workup.ADDITIONwater and toluene were added to it for liquid-liquid separation
5. 5
   洗浄The toluene layer was washed with 3% hydrochloric acid, saturated sodium hydrogencarbonate and water
6. 6
   その他toluene was evaporated away
7. 7
   workup.ADDITIONTo the resulting residue, added
8. 8
   温度this was refluxed for 2 hours
9. 9
   その他Ethanol was evaporated away
10. 10
    workup.ADDITIONthe resulting residue was poured into 500 ml of 5% hydrochloric acid
11. 11
    その他a crystal was thus formed
12. 12
    ろ過The crystal taken out through filtration
13. 13
    その他was recrystallized from a mixed solvent of ethanol and water

実験手順

19 g of ethyl hydroxycinnamate and 7.3 g of potassium hydroxide were added to 150 ml of ethanol, and stirred at 50° C. for 1 hour. This was cooled to 40° C., and 35 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)cinnamic acid (OX6) was obtained. Its melting point was 127.5° C.

出典