Ethylene Glycol → HCID 22086397, compound

HRID 2227262Notes

Reaction equation

HRID 2227262 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 11437716HCID 11437716, compound

Product 1

HCID 22086397HCID 22086397, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-8 (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 1-9 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-88db8e6c45cc45aa9ca24aaf2d0b6b4b
Source dataset
uspto-grants-2002_07
Patent number
US06413955B1

Reaction notes

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