Ethylene Glycol → HCID 57750166, compound

HRID 504535Notes

Reaction equation

HRID 504535 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:11](O)[CH2:12][OH:13]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:7]2[O:13][CH2:12][CH2:11][O:8]2)[CH:9]=1

Participants

5

Reactant 2

HCID 174Ethylene GlycolHCID 124815-Chloro-salicylaldehyde

Product 1

HCID 57750166HCID 57750166, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 5-chloro-2-hydroxybenzaldehyde (20.0 g, 0.128 mol), ethane-1,2-diol (40.0 g, 0.644 mol) and p-toluenesulfonic acid monohydrate (0.44 g, 2.56 mmol) dissolved in toluene (200 mL) was refluxed for 40 h with a dean-stark to remove water. After the reaction mixture was cooled to room temperature, EtOAc (200 mL) was added. Then the organic phase was washed with saturated NaHCO3 solution, dried over anhydrous Na2SO4 and concentrated to give the title compound as a light-yellow solid (24.6 g).

Workup

  1. temperaturewas refluxed for 40 h with a dean-stark
  2. customto remove water
  3. additionEtOAc (200 mL) was added
  4. washThen the organic phase was washed with saturated NaHCO3 solution
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-80924112e04e442a8cea2b88bf115204
Source dataset
uspto-grants-2010_08
Patent number
US07776875B2

Reaction notes

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