Ethylene Glycol → 1-[4-(Ethoxycarbonyl)phenyl]ethanone-ethyleneacetal

HRID 1265214Notes

Reaction equation

HRID 1265214 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1)[CH3:2].[CH2:15](O)[CH2:16][OH:17].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.CCCCCC>C1(C)C=CC=CC=1>[CH2:16]1[O:17][C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:14])=[CH:6][CH:7]=2)([CH3:12])[O:13][CH2:15]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 600911Ethyl 4-acetylbenzoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 186150891-[4-(Ethoxycarbonyl)phenyl]ethanone-ethyleneacetal

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

9.61 g of 4-acetylbenzoic acid ethyl ester (supplied from the firm Wako Pure Chem. Ind.) were dissolved in 200 ml of toluene and thereto were added 20 ml of ethylene glycol and 200 mg of p-toluenesulfonic acid hydrate under argon atmosphere, whereupon the mixture was heated under reflux for 24 hours on Dean-Stark apparatus while removing water. The reaction mixture was then cooled down to room temperature and the toluene layer was washed with water (twice with each 100 ml) and, then, with saturated aqueous sodium chloride solution (100 ml), followed by drying and evaporation to dryness under a reduced pressure, whereby the above-identified compound (12.76 g ) was obtained. Rf=0.58 (ethyl acetate/n-hexane of 1/2).

Workup

  1. temperaturewhereupon the mixture was heated
  2. temperatureunder reflux for 24 hours on Dean-Stark apparatus
  3. customwhile removing water
  4. washthe toluene layer was washed with water (twice with each 100 ml) and, then, with saturated aqueous sodium chloride solution (100 ml)
  5. customby drying
  6. customevaporation to dryness under a reduced pressure, whereby the above-identified compound (12.76 g )
  7. customwas obtained

Sources & evidence

ORD record
ord-4d33a1a66a5040f5b509f023c3a453bc
Source dataset
uspto-grants-2003_04
Patent number
US06545053B1

Reaction notes

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