Ethylene Glycol → HCID 59789669, compound

HRID 499043Notes

Reaction equation

HRID 499043 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1)=[O:2].[CH2:21](O)[CH2:22][OH:23]>C1(C)C=CC=CC=1>[O:2]1[CH2:21][CH2:22][O:23][CH:1]1[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 59789754Diethyl 2-[(3-formylphenyl)methylene]propane-1,3-dioate

Product 1

HCID 59789669HCID 59789669, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The solution of product 32 in toluene, from the previous reaction, is filtered, transferred to a round bottom flask, and ethylene glycol (2.4 eq) is added, followed by p-toulenesulfonic acid (0.5 eq). The reaction mixture is refluxed overnight with a Dean-Stark trap, then cooled down to room temperature, washed with sat. aq NaHCO3, brine, and dried (Na2SO4). Product 33 is not purified further but used as is in the following step.

Workup

  1. filtrationis filtered
  2. customtransferred to a round bottom flask
  3. temperatureThe reaction mixture is refluxed overnight with a Dean-Stark trap
  4. washwashed with sat. aq NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. customProduct 33 is not purified further

Sources & evidence

ORD record
ord-8146d2aaed544a2681dedd2f4845ef91
Source dataset
uspto-grants-2010_08
Patent number
US07767669B2

Reaction notes

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