Acetic Acid → Diethyl 2-(2-naphthyl)malonate

HRID 993074Notes

Reaction equation

HRID 993074 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].[Na].O.C(O)(=O)C.[CH2:23]([O:25][C:26](=O)[O:27]CC)[CH3:24]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([C:26]([O:25][CH2:23][CH3:24])=[O:27])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 7766Diethyl CarbonateHCID 256821Ethyl 2-naphthylacetateHCID 5360545Sodium

Product 1

HCID 15668316Diethyl 2-(2-naphthyl)malonate

Procedure

To a solution of ethyl 2-naphtylacetate (2 g) in 23.3 ml of diethylcarbonate, kept under stirring and at room temperature, are added portionwise 0.232 g of sodium. The reaction mixture is refluxed for 2 hours 30 minutes, then it is concentrated in order to eliminate the not reacted diethylcarbonate and it is added with 20 ml of cold water. The resulting mixture is acidified with acetic acid until weak acidity is reached, then it is extracted three times with diethyl ether. The pooled organic extracts are dried over sodium sulfate and the solvent is evaporated off, to give, after recrystallization from diethyl ether (19 ml), 1.015 g of the product as a white solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 2 hours 30 minutes
  2. concentrationit is concentrated in order
  3. customreacted diethylcarbonate and it
  4. extractionit is extracted three times with diethyl ether
  5. dry with materialThe pooled organic extracts are dried over sodium sulfate
  6. customthe solvent is evaporated off
  7. customto give
  8. customafter recrystallization from diethyl ether (19 ml), 1.015 g of the product as a white solid

Sources & evidence

ORD record
ord-4ec4206765604ab9a956c17eb754fed5
Source dataset
uspto-grants-2002_10
Patent number
US06472396B1

Reaction notes

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