Ethanol → 2-(2-Phenylethyl)malonic acid

HRID 356874Notes

Reaction equation

HRID 356874 reaction equation
[CH2:1]([CH2:8][CH:9]([C:15]([O:17]CC)=[O:16])[C:10]([O:12]CC)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[K+]>O>[CH2:1]([CH2:8][CH:9]([C:15]([OH:17])=[O:16])[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 811191,3-Diethyl 2-(2-phenylethyl)propanedioate

Product 1

HCID 1012342-(2-Phenylethyl)malonic acidYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The diethyl benzylmethylmalonate (75 g) was combined with 300 ml of ethanol and a solution of 100 g potassium hydroxide in 300 ml of water and heated to a gentle reflux for 5 hours. After cooling, the mixture was extracted with diethyl ether (2×300 ml). The aqueous phase was then acidified with 120 ml concentrated hydrochloric acid, and extracted with diethyl ether (3×300 ml). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to yield 49.2 g of benzylmethylmalonic acid as a yellow solid (83% yield).

Workup

  1. temperaturea gentle reflux for 5 hours
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with diethyl ether (2×300 ml)
  4. extractionextracted with diethyl ether (3×300 ml)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-64f66f15122b4aee823bd86f5b9c991e
Source dataset
uspto-grants-1998_11
Patent number
US05840729

Reaction notes

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