Ethylene Glycol → HCID 69287399, compound

HRID 2116435Notes

Reaction equation

HRID 2116435 reaction equation
C(C1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=CC=1)=C.[CH2:11](O)[CH2:12]O.[OH2:15].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:8]=[C:7]1[CH2:6][CH2:9][C:10](=[O:15])[CH:22]1[C:16]1[CH:21]=[CH:20][C:19]([CH:11]=[CH2:12])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 1140TolueneHCID 393894-Vinylbenzaldehyde

Product 1

HCID 69287399HCID 69287399, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

In 170 mL of toluene were dissolved 17.38 g of 4-vinylbenzaldehyde and 10.89 g of ethylene glycol. To the solution were added 0.25 g of p-toluenesulfonic acid monohydrate and 0.22 g of p-hydroquinene, and the mixture was heated at reflux. Water generated during the reaction was removed by a Dean-Stark trap. After 8 hours, it was allowed to be cooled and evaporated under a reduced pressure. The residue was distilled under vacuum (92 to 93° C./0.45 mmHg), to give 13.44 g of 4-(2,5-dioxocyclopentyl)styrene (yield: 58%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customwas removed by a Dean-Stark trap
  4. temperatureto be cooled
  5. customevaporated under a reduced pressure
  6. distillationThe residue was distilled under vacuum (92 to 93° C./0.45 mmHg)

Sources & evidence

ORD record
ord-86faf18d56974b5c88066a8636710bb9
Source dataset
uspto-grants-2008_10
Patent number
US07439005B2

Reaction notes

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