Ethylene Glycol → HCID 59428066, compound

HRID 658927Notes

Reaction equation

HRID 658927 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[CH:17]=[O:18])[CH2:6][CH2:7][CH3:8])[CH3:2].[CH2:20](O)[CH2:21][OH:22]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[CH:17]1[O:22][CH2:21][CH2:20][O:18]1)[CH2:6][CH2:7][CH3:8])[CH3:2]

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 594280852-(4-Chloro-2-formyl-phenoxy)-pentanoic acid ethyl ester

Product 1

HCID 59428066HCID 59428066, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-chloro-2-formyl-phenoxy)-pentanoic acid ethyl ester (15 g, 53 mmol), ethylene glycol (25 mL, 440 mmol) and p-toluenesulfonic acid (0.8 g, 4.65 mmol) in toluene (150 mL) was refluxed with a Dean-Stark trap attached to remove water. After 3 h, the reaction was cooled and washed with water, saturated NaHCO3 solution and water, dried over anhydrous Na2SO4 and concentrated to give the title compound as a light yellow oil (16 g).

Workup

  1. temperaturewas refluxed with a Dean-Stark trap
  2. customto remove water
  3. temperaturethe reaction was cooled
  4. washwashed with water, saturated NaHCO3 solution and water
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5612fbe8190d410192fcd38df5f305ae
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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