반응 #362585

반응 방정식

hydrochloric acid

1,1-Dimethylethyl-4-mercaptophenol

sodium methoxide

cyclopentene oxide

→

product

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

용매

brine

methanol

water

반응 조건

후처리

1. 1
   workup.WAITAfter several minutes
2. 2
   추출The mixture was extracted twice with 100 ml of diethyl ether
3. 3
   건조The combined diethyl ether extracts were dried over anhydrous magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated to an oil with a rotary evaporator
6. 6
   기타The product was purified by silica gel chromatography

실험 절차

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.

출처