Ethylene Glycol → HCID 20674639, compound

HRID 1387444Notes

Reaction equation

HRID 1387444 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](O)[CH2:24][OH:25].CC1C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>CCOC(C)=O.O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:22])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]1([CH3:20])[O:25][CH2:24][CH2:23][O:21]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 21968719HCID 21968719, compound

Product 1

HCID 20674639HCID 20674639, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ketone 7-2 (695 mmol), ethylene glycol (59 ml, 1040 mmol), p-TSA (500 mg, 2.713 mmol) and benzene (2000 mL) was heated to reflux with azeotropic removal of water for 12 hours. The reaction mixture was diluted with EtOAc and then washed with sat. NaHCO3, brine, dried (MgSO4), and concentrated to give 7-3 as a yellow oil.

Workup

  1. temperaturewas heated
  2. washwashed with sat. NaHCO3, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-441a3e7bbb964a589cd482aba3545cd7
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

Loading…