Reaktion #6786

Reaktionsgleichung

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

Ausbeute 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

Ausbeute 99.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGfurther stirred at room temperature for 3 h
2. 2
   SonstigeThe solvent was removed under vacuum
3. 3
   workup.DISSOLUTIONThe residue was dissolved in oil
4. 4
   ExtraktionHCl and extracted by ethylacetate
5. 5
   WaschenThe combined organic phase was washed successively with saturated NaHCO3 solution, water and brine
6. 6
   Trocknenthen dried over Na2SO4
7. 7
   SonstigeEvaporation of organic phase

Vorschrift

A solution of 4-methylbenzenethiol (5 g, 40.25) in dry THF was added dropwise to a suspension of NaH (60% in mineral oil, 1.98 g, 48.30) in THF at room temperature and stirred for 30 min. under N2 atmosphere. Ethylbromoacetate (4.9 mL, 44.27) was added slowly to this solution and further stirred at room temperature for 3 h. The solvent was removed under vacuum. The residue was dissolved in oil. HCl and extracted by ethylacetate. The combined organic phase was washed successively with saturated NaHCO3 solution, water and brine then dried over Na2SO4. Evaporation of organic phase yielded 8.46 g (99%) colorless oil. 1H NMR (CDCl3): δ 1.22 (t, J=7.2 Hz, 3H), 2.32 (s, 3H), 3.57 (s, 2H), 4.14 (q, J=7.2 Hz, 2H), 7.11 (d, J=8.0 Hz, 2H), 7.33 (d, J=8.0 Hz, 2H). EIMS m/z 210 (M+1), 233 (M+23).

Quelle