反応 #362587

反応方程式

Mercaptoacetic acid

sodium methoxide

cyclohexene oxide

→

product

trans-[(2-Hydroxycyclohexyl)thio]acetic acid

溶媒

methanol

反応条件

後処理

1. 1
   温度cooled by an ice bath
2. 2
   その他The ice bath was removed
3. 3
   workup.ADDITIONwas poured into water (250 ml)
4. 4
   workup.ADDITIONcontaining concentrated hydrochloric acid (50 ml) and brine (200 ml)
5. 5
   抽出The reaction mixture was extracted three times with 150 ml of diethyl ether
6. 6
   洗浄The combined diethyl ether extracts were washed twice with 50 ml of brine
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated with a rotary evaporator

実験手順

Mercaptoacetic acid (18.5 g), 0.20 mole) was added to methanol (125 ml) containing sodium methoxide [prepared from sodium (9.3 g, 0.40 mole)] cooled by an ice bath. After 20 minutes, cyclohexene oxide was added slowly during 20 minutes. The ice bath was removed, and the reaction mixture was stirred at room temperature for 4 hours at which time it was poured into water (250 ml) containing concentrated hydrochloric acid (50 ml) and brine (200 ml). The reaction mixture was extracted three times with 150 ml of diethyl ether. The combined diethyl ether extracts were washed twice with 50 ml of brine, dried over anhydrous magnesium sulfate, filtered and concentrated with a rotary evaporator to give the product as an oil. The structure was supported by NMR.

出典