Ethylene Glycol → 2-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-butyric acid methyl ester

HRID 504554Notes

Reaction equation

HRID 504554 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH:15]=[O:16])[CH2:5][CH3:6].[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:17])[CH:4]([O:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH:15]1[O:20][CH2:19][CH2:18][O:16]1)[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 594280922-(4-Chloro-2-formyl-phenoxy)-butyric acid methyl ester

Product 1

HCID 594280712-(4-Chloro-2-[1,3]dioxolan-2-yl-phenoxy)-butyric acid methyl esterYield 68.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-chloro-2-formyl-phenoxy)-butyric acid methyl ester (50 g, 0.195 mol), ethylene glycol (89 mL, 1.56 mol) and p-toluenesulfonic acid (2.8 g, 16.5 mmol) in toluene (400 mL) was refluxed with a Dean-Stark trap attached to remove the water. After 3 h, the reaction was cooled and washed with water, saturated NaHCO3 and water, dried over anhydrous Na2SO4 and concentrated to give the title compound as a light yellow oil (40 g).

Workup

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

Sources & evidence

ORD record
ord-5d209522ac3b408986648d61bfec3015
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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