Malonic Acid → HCID 11172599, compound

HRID 899017Notes

Reaction equation

HRID 899017 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[CH2:8](O)[C:9]([CH3:12])([CH3:11])[CH3:10].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[C:1]([O:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:6])[CH2:2][C:3]([O:5][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:4]

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 6404Neopentyl alcohol

Product 1

HCID 11172599HCID 11172599, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Malonic acid (40 g, 0.38 mol) and neopentyl alcohol (77.5 g, 0.88 mol) in 110 ml of toluene in the presence of 0.2 ml of concentrated sulfuric acid are refluxed for 3 hours in a reactor equipped with Dean-Stark apparatus. The water formed is removed azeotropically. The organic phase is washed 3 times with water and dried over sodium sulfate. After filtration and evaporation of the solvent under vacuum, 88 g (yield: 94%) of dineopentyl malonate are obtained in the form of a colorless oil and used without further purification in the next step.

Workup

  1. customequipped with Dean-Stark apparatus
  2. customis removed azeotropically
  3. washThe organic phase is washed 3 times with water
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-d61f873dd3e84a3fa3b421d90f2c0a80
Source dataset
uspto-grants-2008_04
Patent number
US07354571B2

Reaction notes

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