Reaction #6786

Reaction equation

4-methylbenzenethiol

NaH

Ethylbromoacetate

→

colorless oil

Yield 99.0%

p-Tolylsulfanyl-acetic acid ethyl ester

Yield 99.0%

Solvents

THF

THF

Conditions

Workup

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

Procedure

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).

Source