反応 #2304290

反応方程式

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

ethyl hydroxybenzoate

potassium hydroxide

dimethylformamide

→

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

収率 84.4%

溶媒

toluene

Water

反応条件

後処理

1. 1
   温度This was cooled to 45° C.
2. 2
   workup.STIRRINGKept at 45° C., this was stirred for 3 hours
3. 3
   洗浄The toluene layer was washed with 3% hydrochloric acid, saturated sodium hydrogencarbonate and water
4. 4
   その他toluene was evaporated away
5. 5
   workup.ADDITIONTo the resulting residue, added
6. 6
   温度this was refluxed for 2 hours
7. 7
   その他Ethanol was evaporated away
8. 8
   workup.ADDITIONthe resulting residue was poured into 500 ml of 5% hydrochloric acid
9. 9
   その他a crystal was thus formed
10. 10
    ろ過The crystal taken out through filtration
11. 11
    その他was recrystallized from a mixed solvent of ethanol and water

実験手順

50 g of ethyl hydroxybenzoate and 21 g of potassium hydroxide were added to 400 ml of dimethylformamide, and stirred at 70° C. for 1 hour. This was cooled to 45° C., and 100 g of 3-[(tosyloxy)methyl]-3-ethyloxetane was dropwise added to it. Kept at 45° C., this was stirred for 3 hours. 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 50 g of sodium hydroxide, 500 ml of ethanol and 200 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 60 g of 4-(3-ethyloxetan-3-ylmethoxy)benzoic acid (OX5) was obtained. Its melting point was 127.5° C.

出典