Ethylene Glycol → HCID 15521920, compound

HRID 850591Notes

Reaction equation

HRID 850591 reaction equation
[CH3:1][O:2][N:3]([CH3:11])[C:4](=[O:10])[CH2:5][CH2:6][C:7](=[O:9])[CH3:8].[CH2:12](O)[CH2:13][OH:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[CH3:1][O:2][N:3]([CH3:11])[C:4](=[O:10])[CH2:5][CH2:6][C:7]1([CH3:8])[O:14][CH2:13][CH2:12][O:9]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 15521919HCID 15521919, compound

Product 1

HCID 15521920HCID 15521920, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 2-1 (38 g, 0.239 mol) in 500 mL benzene was added ethylene glycol (17.3 mL, 0.310 mol) and p-toluenesulfonic acid (1 g). The mixture was heated at reflux for 2 h with azeotropic removal of water. After cooling, the solution was washed with 200 mL sat. NaHCO3, brine, and dried over Na2SO4. Evaporative removal of the solvent gave 2-2 as a yellow oil. TLC Rf =0.62 (silica, ethyl acetate). 1H NMR (300 MHz, CDCl3) δ 3.95 (m, 4H), 3.68 (s, 3H), 3.17 (s, 3H), 2.51 (t, 2H, J=8 Hz), 2.00 (t, 3H, J=6 Hz) 1.33 (S, 3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureAfter cooling
  3. washthe solution was washed with 200 mL sat. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. customEvaporative removal of the solvent

Sources & evidence

ORD record
ord-b412a49f65444067ab9637e59bd18ed4
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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