Diethyl Malonate → HCID 12932092, compound

HRID 2285744Notes

Reaction equation

HRID 2285744 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].CC[O-].[Na+].[Na].[Cl:17][C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:21]=[CH:22][CH:23]=1>O.C(O)C>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([CH2:26][CH2:25][CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([Cl:17])[CH:19]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 54285611HCID 54285611, compound

Product 1

HCID 12932092HCID 12932092, compoundYield 41.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

91.3 g of malonic acid diethyl ester are added dropwise, at 50° C., to a sodium ethylate solution freshly prepared from 13.11 g of sodium and 650 ml of ethanol. The mixture is kept at that temperature for 2.5 hours, and 185 g of p-toluenesulfonic acid [3-(3-chlorophenyl)propyl] ester are then added dropwise. When the addition is complete, the obtained mixture is stirred at 50° C. for 6 hours; 800 ml of water are then added, and the mixture is extracted 3 times with a total of 1 liter of diethyl ether. The combined organic phases are dried over sodium sulfate; the solvent is evaporated off, and the residue is distilled. 74.2 g of 3-(3-chlorophenyl)propylmalonic acid diethyl ester (b.p. 145° to 152° C. under 0.01 mm Hg) are obtained.

Workup

  1. additionWhen the addition
  2. extractionthe mixture is extracted 3 times with a total of 1 liter of diethyl ether
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent is evaporated off
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-cd9c290a66f94175936c90898f2c54ba
Source dataset
uspto-grants-1982_04
Patent number
US04324796

Reaction notes

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