Ethylene Glycol → HCID 59789669, compound

HRID 30448Notes

Reaction equation

HRID 30448 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-b2293f481fac4e9ebe40fbfcb33a65e9
Source dataset
uspto-grants-2008_09
Patent number
US07423148B2

Reaction notes

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