Reacción #362587

Ecuación de reacción

Mercaptoacetic acid

sodium methoxide

cyclohexene oxide

→

product

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

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled by an ice bath
2. 2
   OtroThe 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
   ExtracciónThe reaction mixture was extracted three times with 150 ml of diethyl ether
6. 6
   LavadoThe combined diethyl ether extracts were washed twice with 50 ml of brine
7. 7
   Secadodried over anhydrous magnesium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated with a rotary evaporator

Procedimiento

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.

Fuente