Réaction #362587

Équation de réaction

Mercaptoacetic acid

sodium methoxide

cyclohexene oxide

→

product

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

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   Températurecooled by an ice bath
2. 2
   AutreThe 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
   ExtractionThe reaction mixture was extracted three times with 150 ml of diethyl ether
6. 6
   LavageThe combined diethyl ether extracts were washed twice with 50 ml of brine
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated with a rotary evaporator

Mode opératoire

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.

Source