Ethanol → Diethyl 2-phenylbutanedioate

HRID 45246Notes

Reaction equation

HRID 45246 reaction equation
[C:1]1([CH:7]([CH2:11][C:12]([OH:14])=[O:13])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OS(O)(=O)=O.[C:20]1(C)C=CC=C[CH:21]=1.[CH3:27][CH2:28]O>>[C:1]1([CH:7]([CH2:11][C:12]([O:14][CH2:27][CH3:28])=[O:13])[C:8]([O:10][CH2:20][CH3:21])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1140TolueneHCID 95459Phenylsuccinic acid

Product 1

HCID 249294Diethyl 2-phenylbutanedioateYield 46%

Procedure

In Dean-Stark apparatus, a mixture of 37 g (190.5 mmol) of 2-phenylbutanedioic acid, 6 mL of conc. H2SO4, 80 mL of toluene and 80 mL of EtOH is refluxed for 72 hours. After cooling to room temperature, the reaction mixture is concentrated under reduced pressure and then treated with 300 mL of water, and extracted with Et2O (2×400 mL). The organic phases are combined, dried over Na2SO4, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc. 22 g of diethyl 2-phenylbutanedioate are obtained in the form of an oil.

Workup

  1. temperatureis refluxed for 72 hours
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. additiontreated with 300 mL of water
  4. extractionextracted with Et2O (2×400 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customis purified by chromatography on a column of silica gel
  10. washeluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc

Sources & evidence

ORD record
ord-fdec76125d1d419891494a104e788ff4
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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