Réaction #6613

Équation de réaction

sodium periodate

thioether

4-Carboxybenzyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl thioether

hydrochloric acid

→

title compound

Rendement 39.6%

4-Carboxybenzyl 5,6,7,-8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl sulfoxide

Rendement 39.6%

Solvants

water

water

ethanol

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted with dichloromethane
2. 2
   Lavagethe organic extracts were washed with water
3. 3
   Séchagedried over magnesium sulfate
4. 4
   Autreevaporated under reduced pressure
5. 5
   AutreCrystallization of the oily residue from ethanol

Mode opératoire

A solution of 3.4 g (16 mmol) of sodium periodate in 30 ml of water was added dropwise to 5.3 g (15 mmol) of the thioether from Example 10 in a mixture of 150 ml of ethanol and 40 ml of dimethylformamide at 0° C., and the mixture was then stirred at the same temperature for 2 hours and at room temperature overnight. The reaction solution was then poured into water, the pH was adjusted to 5 with 2N hydrochloric acid, the mixture was extracted with dichloromethane, and the organic extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure. Crystallization of the oily residue from ethanol yielded 2.2 g of title compound of melting point 198°-200° C.

Source