Diethyl Malonate → HCID 54537439, compound

HRID 1156177Notes

Reaction equation

HRID 1156177 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:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:20][CH:19]=1>O.C(O)C>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([CH2:26][CH2:25][CH2:24][C:21]1[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 18411848HCID 18411848, compound

Product 1

HCID 54537439HCID 54537439, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

108.5 g of malonic acid diethyl ester are added dropwise, at 50°, to a sodium ethylate solution freshly prepared from 15.6 g of sodium and 750 ml of ethanol. The mixture is kept at the above temperature for 2.5 hours and 220 g of p-toluenesulphonic acid 3-(4-chlorophenyl)-propyl ester are then added dropwise. After the addition, the mixture is stirred at 50° 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 sulphate, the solvent is evaporated off and the residue is distilled. 105.6 g of 3-(4-chlorophenyl)-propylmalonic acid diethyl ester of b.p. 145°-155° under 0.01 mm Hg (1.33 Pa) are obtained.

Workup

  1. additionAfter 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 sulphate
  4. customthe solvent is evaporated off
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-b4a345b80d1241538355f2dc4b503d00
Source dataset
uspto-grants-1982_06
Patent number
US04334089

Reaction notes

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