p-Toluenesulfonic acid → 2-Ethylhexyl syringate

HRID 1153686Notes

Reaction equation

HRID 1153686 reaction equation
[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2].[C:10](O)(=[O:22])[C:11]1[CH:21]=[C:18]([O:19][CH3:20])[C:16]([OH:17])=[C:13]([O:14][CH3:15])[CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:10]([O:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:6][CH2:7][CH2:8][CH3:9])(=[O:22])[C:11]1[CH:12]=[C:13]([O:14][CH3:15])[C:16]([OH:17])=[C:18]([O:19][CH3:20])[CH:21]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 77202-EthylhexanolHCID 10742Syringic Acid

Product 1

HCID 1805932-Ethylhexyl syringate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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%.

Workup

  1. temperaturewith reflux condenser
  2. temperatureThe mixture was refluxed for 20 h
  3. distillationExcess alcohol and toluene were distilled off under slight vacuum
  4. additionThe dark liquid residue was diluted with CH2Cl2
  5. extractionextracted with 2% NaHCO3 +15% aqueous NaCl
  6. dry with materialThe organic layer was dried with anhydrous Na2SO4
  7. distillationdistilled
  8. customAfter removal of all unreacted 2-ethylhexanol the product
  9. distillationdistilled over as a viscous, colorless liquid, b.p. 204°-209° C./4×102Pa, which
  10. customcrystallized
  11. customon standing at room temperature to a fine white solid, mp 35°-36° C

Sources & evidence

ORD record
ord-2aa03a303f4c4afb9e8741f3dcdd2ee4
Source dataset
uspto-grants-1984_12
Patent number
US04486179

Reaction notes

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