Reaktion #2380063

Reaktionsgleichung

bicarbonate

2,6-di-t-butylphenol

2-(methylthio)acetic acid

TFAA

→

1-(3,5-di-t-butyl-4-hydroxyphenyl)-2-(methylsulfanyl)ethanone

Lösungsmittel

EtOAc

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis then added
2. 2
   workup.ADDITIONis added via syringe at a fast rate
3. 3
   workup.ADDITIONA small amount of CH2C12 is added to aid
4. 4
   workup.ADDITIONin mixing
5. 5
   SonstigeThe reaction quickly turns violet
6. 6
   Extraktionextracted with 2 portions of Et2O
7. 7
   WaschenThe combined organics are washed with brine
8. 8
   Filtrationfiltered through cotton
9. 9
   Sonstigedried over molecular sieves
10. 10
    Einengenconcentrated on a rotavap
11. 11
    Sonstigedried under vacuum
12. 12
    SonstigeThis gives a white solid which
13. 13
    Sonstigecan be crystallized from EtOAc/hexanes
14. 14
    Sonstigeto give orange crystals, mp=108.5°-109.5° C.

Vorschrift

2,6-di-t-butylphenol (1.7680 g, 8.66mmol) is placed in a flame dried RBF, and 2-(methylthio)acetic acid (0.80 mL, 9.19 mmol) is then added. This is then blanketed with argon and TFAA (1.30 mL, 9.20 mmol) is added via syringe at a fast rate. A small amount of CH2C12 is added to aid in mixing. The reaction quickly turns violet and darkens. It is followed by TLC using 10% EtOAc in hexanes. After 5 h, the reaction is carefully poured into 70 mL saturated bicarbonate and extracted with 2 portions of Et2O. The combined organics are washed with brine, filtered through cotton, dried over molecular sieves, then concentrated on a rotavap and dried under vacuum. This gives a white solid which can be crystallized from EtOAc/hexanes to give orange crystals, mp=108.5°-109.5° C.

Quelle