Reaktion #951836

Reaktionsgleichung

hydrochloric acid

5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinone

sodium hydroxide

→

subtitled intermediate

3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-2-mercaptopropanoic acid

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux temperature over the course of one hour
2. 2
   Temperaturmaintained
3. 3
   Temperaturat reflux for 2 hours
4. 4
   Sonstigethe temperature of the mixture below 16° C
5. 5
   workup.DISSOLUTIONThe resultant solid was dissolved
6. 6
   SonstigeThe organic layer was separated
7. 7
   Waschenwashed 3 times with 100 ml of saturated sodium chloride solution
8. 8
   Trocknendried over sodium sulfate
9. 9
   Sonstigethe solvent was removed in vacuo
10. 10
    Sonstigeto yield

Vorschrift

To 114.5 g of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-thioxo-4-thiazolidinone, 815 ml of 2M sodium hydroxide was added. The resultant mixture was heated to reflux temperature over the course of one hour and maintained at reflux for 2 hours. The mixture was cooled in an ice/water bath to 15° C. and 290 ml of 6M hydrochloric acid was added dropwise under a nitrogen atmosphere over 15 minutes, keeping the temperature of the mixture below 16° C. The resultant solid was dissolved by adding 600 ml of ethyl acetate to the mixture. The organic layer was separated, washed 3 times with 100 ml of saturated sodium chloride solution, dried over sodium sulfate and then the solvent was removed in vacuo to yield 100.3 g (100% of yield) of the subtitled intermediate. mp 137°-140° C.

Quelle