Malonic Acid → HCID 11172599, compound

HRID 1351713Notes

Reaction equation

HRID 1351713 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) are refluxed for 3 hours in 110 ml of toluene in the presence of 0.2 ml of concentrated sulfuric acid 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 (94% yield) of dineopentyl malonate are obtained in the form of a colorless oil, and are used in the next step without further purification.

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-08a33d694bf0485a85bed03e05e6d99d
Source dataset
uspto-grants-2007_05
Patent number
US07217821B2

Reaction notes

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