p-Toluenesulfonic acid → 2-Ethylhexyl syringate

Participants

Reaction Steps

To 13.2 g (0.1 mol) 2-ethyl-1-hexanol in a flask equipped with reflux condenser connected to a Dean-Stark trap was added 9.9 g (0.05 mol) syringic acid, 0.2 g p-toluenesulfonic acid and 75 ml toluene. The mixture was refluxed for 20 h. Excess alcohol and toluene were distilled off under slight vacuum. The dark liquid residue was diluted with CH2Cl2 and extracted with 2% NaHCO3 +15% aqueous NaCl followed by neutral 15% aqueous NaCl solution. The organic layer was dried with anhydrous Na2SO4 and distilled. After removal of all unreacted 2-ethylhexanol the product distilled over as a viscous, colorless liquid, b.p. 204°-209° C./4×102Pa, which crystallized on standing at room temperature to a fine white solid, mp 35°-36° C. Yield: 10.1 g, 65%.

Provenance & Evidence