Ethanol → Phenylsuccinic acid

HRID 45245Notes

Reaction equation

HRID 45245 reaction equation
[C:1]([CH:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:4][C:5]([O:7]CC)=[O:6])#N.[OH-:16].[K+].CC[OH:20]>C1(C)C=CC=CC=1>[C:10]1([CH:3]([CH2:4][C:5]([OH:7])=[O:6])[C:1]([OH:20])=[O:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 12414061Ethyl 3-cyano-3-phenylpropanoate

Product 1

HCID 95459Phenylsuccinic acidYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 43.5 g (214 mmol) of ethyl 3-cyano-3-phenylpropanoate and 52.2 g (930.4 mmol) of potassium hydroxide in 670 mL of EtOH is refluxed for 4 hours. After cooling to room temperature, the medium is concentrated under vacuum and then treated with 1 L of 1N HCl, and a precipitate then forms, which is filtered off and rinsed with water (2×50 mL). The solid obtained is taken up in a mixture of 200 mL of toluene and 40 mL of EtOH and concentrated under reduced pressure, and then dried with a vane pump. 37 g of 2-phenylbutanedioic acid are obtained in the form of a solid, which is used without further purification in the following step.

Workup

  1. temperatureis refluxed for 4 hours
  2. concentrationthe medium is concentrated under vacuum
  3. additiontreated with 1 L of 1N HCl
  4. filtrationwhich is filtered off
  5. washrinsed with water (2×50 mL)
  6. customThe solid obtained
  7. concentrationconcentrated under reduced pressure
  8. customdried with a vane pump

Sources & evidence

ORD record
ord-9606fc799fc148db8f11487efd069dc2
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

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