Reaction #587474

Reaction equation

p-toluenesulfonyl chloride

2-ethylhexanol

hydrochloric acid

→

2-ethylhexyl p-toluenesulfonate

Yield 87.5%

Solvents

pyridine

Conditions

Workup

1. 1
   workup.ADDITIONadded
2. 2
   workup.WAITthe resulting mixture was left at 0° C.
3. 3
   Temperaturewhile cooled overnight
4. 4
   Extractionthe product was extracted with ethyl acetate
5. 5
   Washand the organic layer was washed with 1N hydrochloric acid until the aqueous hydrochloric acid layer
6. 6
   DryingThe organic layer was dried over magnesium sulfate
7. 7
   Otherevaporated

Procedure

In a 1-L round-bottomed flask containing 250 mL of pyridine, added was 75 g of p-toluenesulfonyl chloride. After the reaction solution was cooled to 0° C., 34 g of 2-ethylhexanol was added dropwise over 30 minutes, and the resulting mixture was left at 0° C. while cooled overnight. The reaction solution was poured into cold 1N hydrochloric acid; the product was extracted with ethyl acetate; and the organic layer was washed with 1N hydrochloric acid until the aqueous hydrochloric acid layer became acidic. The organic layer was dried over magnesium sulfate and evaporated, to give 65 g of 2-ethylhexyl p-toluenesulfonate. The fact that the product is the desirable compound was confirmed with NMR, IR, and mass spectrometry spectra.

Source