Réaction #362589

Équation de réaction

hydrochloric acid

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol

sodium ethoxide

Cyclohexene oxide

→

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

Solvants

ethyl alcohol

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted twice with 200 ml of ethyl ether
2. 2
   LavageThe combined ethyl ether extracts were washed twice with 25 ml of water
3. 3
   Séchagedried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo to a yellow oil
6. 6
   AutreThe product was purified by silica
7. 7
   Autreget chromatography
8. 8
   Autrerecrystallized from methyl alcohol/water, m.p. ca 91° C

Mode opératoire

2,6-bis(1,1-Dimethylethyl)-4-mercaptophenol (12.8 g, 0.054 moles) was added to a solution of sodium ethoxide [prepared from sodium (2.5 g, 0.108 mole)] in ethyl alcohol (75 ml). Cyclohexene oxide (5.15 g, 0.0525 mole) was added and the reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into 10% hydrochloric acid (250 ml) and the mixture was extracted twice with 200 ml of ethyl ether. The combined ethyl ether extracts were washed twice with 25 ml of water, dried over magnesium sulfate, filtered and concentrated in vacuo to a yellow oil. The product was purified by silica get chromatography and recrystallized from methyl alcohol/water, m.p. ca 91° C. The structure was supported by NMR, infrared spectroscopy, and elemental analysis.

Source