Reacción #362589

Ecuación de reacción

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

Disolventes

ethyl alcohol

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted twice with 200 ml of ethyl ether
2. 2
   LavadoThe combined ethyl ether extracts were washed twice with 25 ml of water
3. 3
   Secadodried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo to a yellow oil
6. 6
   OtroThe product was purified by silica
7. 7
   Otroget chromatography
8. 8
   Otrorecrystallized from methyl alcohol/water, m.p. ca 91° C

Procedimiento

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.

Fuente