Ethylene Glycol → HCID 86743898, compound

HRID 1650173Notes

Reaction equation

HRID 1650173 reaction equation
[C:1]([CH:3]1[C:8](=[O:9])[CH:7]([CH3:10])[CH2:6][N:5]([C:11]([O:13][CH3:14])=O)[CH2:4]1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:26]([OH:29])[CH2:27][OH:28].ClC(Cl)(Cl)C>O>[CH2:26]1[O:29][C:11]([N:5]2[CH2:6][CH:7]([CH3:10])[C:8](=[O:9])[CH:3]([C:1]#[N:2])[CH2:4]2)([O:13][CH3:14])[O:28][CH2:27]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 62781,1,1-TrichloroethaneHCID 23052457HCID 23052457, compound

Product 1

HCID 86743898HCID 86743898, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of crude 11 (200 g, 1.02 mol), 4-toluenesulfonic acid (35 g), 1,2-ethanediol (900 ml), and 1,1,1-trichlorethane (1 liter) was refluxed with a water separator overnight. The mixture was cooled, water (1 liter) was added and the phases separated. The aqueous phase was extracted 3 times with dichloromethane, and the combined organic phases were washed once with dilute sodium hydroxide solution and once with saturated sodium chloride solution. Drying over magnesium sulphate and evaporation in vacuo of the organic phase yielded 12 (195 g, 80%) as an oil.

Workup

  1. temperatureThe mixture was cooled
  2. customthe phases separated
  3. extractionThe aqueous phase was extracted 3 times with dichloromethane
  4. washthe combined organic phases were washed once with dilute sodium hydroxide solution and once with saturated sodium chloride solution
  5. dry with materialDrying over magnesium sulphate and evaporation in vacuo of the organic phase

Sources & evidence

ORD record
ord-9d4144469694499c9bf0ffcc4fb2a2c4
Source dataset
uspto-grants-1990_05
Patent number
US04923880

Reaction notes

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