Ethylene Glycol → 96648-14-5

HRID 2309134Notes

Reaction equation

HRID 2309134 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]1([CH3:15])[CH:10]=[CH:9][C:8](S(O)(=O)=O)=[CH:7][CH:6]=1.[CH:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:22](=[O:25])(O)[O-:23].[Na+].CC[O:29][CH2:30][CH3:31]>>[CH2:2]1[CH2:1][O:4][C:8]2([CH2:7][C@H:6]3[C@H:10]([CH2:5][C@@H:15]([O:23][C:22](=[O:25])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C@@H:31]3[CH2:30][OH:29])[CH2:9]2)[O:3]1

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 241BenzeneHCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 2282207396648-14-5

Procedure

320 mg. of the alcohol prepared according to Reference Example 1(o), 0.5 ml. of ethylene glycol, 4 mg. of p-toluenesulfonic acid, and 10 ml. of benzene are agitated for 1.5 hours with the use of a water trap at reflux temperature. The mixture is cooled, diluted with ether, shaken once with 4% sodium bicarbonate solution, washed neutral with water, dried over magnesium sulfate, and evaporated under vacuum, thus obtaining 390 mg. of the ketal as a colorless oil.

Workup

  1. temperatureat reflux temperature
  2. temperatureThe mixture is cooled
  3. washwashed neutral with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under vacuum
  6. customthus obtaining 390 mg

Sources & evidence

ORD record
ord-816a39d162bb4cf8af99d4f913107364
Source dataset
uspto-grants-1987_09
Patent number
US04692464

Reaction notes

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