反応 #362585

反応方程式

hydrochloric acid

1,1-Dimethylethyl-4-mercaptophenol

sodium methoxide

cyclopentene oxide

→

product

trans-2,6-bis(1,1-Dimethylethyl)-4-[(2-hydroxycyclopentyl)thio]phenol

溶媒

brine

methanol

water

反応条件

後処理

1. 1
   workup.WAITAfter several minutes
2. 2
   抽出The mixture was extracted twice with 100 ml of diethyl ether
3. 3
   乾燥The combined diethyl ether extracts were dried over anhydrous magnesium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated to an oil with a rotary evaporator
6. 6
   その他The product was purified by silica gel chromatography

実験手順

2.6-bis(1,1-Dimethylethyl-4-mercaptophenol (11.5 g, 0.048 mole) was added to a solution of sodium methoxide [prepared from sodium (2.2 g, 0.097 mole)] in methanol (75 ml). After several minutes, cyclopentene oxide (3.86 g, 0.046 mole) was added, and the reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into water (100 ml) containing saturated brine (50 ml) and 1N hydrochloric acid (80 ml). The mixture was extracted twice with 100 ml of diethyl ether. The combined diethyl ether extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to an oil with a rotary evaporator. The product was purified by silica gel chromatography to give the product as a white solid which was recrystallized from hexane (DSC.m.p. 90° C.). The structure was supported by NMR and elemental analysis.

出典