Ethylene Glycol → HCID 22086394, compound

HRID 2227269Notes

Reaction equation

HRID 2227269 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:21])[CH2:15][CH2:16][CH2:17][C:18](=[O:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:22](O)[CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:21])[CH2:15][CH2:16][CH2:17][C:18]1([CH3:19])[O:24][CH2:23][CH2:22][O:20]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 22086388HCID 22086388, compound

Product 1

HCID 22086394HCID 22086394, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-1 (45 g, 156 mmol) and ethylene glycol (13.0 mL, 223 mmol) in benzene (500 mL) was added catalytic p-toluenesulfonic acid (125 mg). The resulting mixture was heated at strong reflux with azeotropic removal of water for 4 h. The mixture was cooled to ambient temperature, diluted with ethyl acetate and washed with water, saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated at reduced pressure to give 2-2 as a yellow oil, which crystallized on standing.

Workup

  1. temperatureThe resulting mixture was heated
  2. washwashed with water, saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-58c302777c834a6da3e2e75208cc1be7
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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