Malonic Acid → Bis(4-methylpentan-2-yl) propanedioate

HRID 1351714Notes

Reaction equation

HRID 1351714 reaction equation
[C:1]([OH:7])(=[O:6])[CH2:2][C:3]([OH:5])=[O:4].[CH3:8][CH:9]([CH2:11][CH:12](O)[CH3:13])[CH3:10].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[C:1]([O:7][CH:12]([CH3:13])[CH2:11][CH:9]([CH3:10])[CH3:8])(=[O:6])[CH2:2][C:3]([O:5][CH:12]([CH3:13])[CH2:11][CH:9]([CH3:10])[CH3:8])=[O:4]

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 962WaterHCID 1118Sulfuric AcidHCID 79104-Methyl-2-Pentanol

Product 1

HCID 57451657Bis(4-methylpentan-2-yl) propanedioateYield 83.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Malonic acid (72.8 g, 0.7 mol) and 2-methyl-4-pentanol(286 g, 2.8 mol) in 200 ml of toluene are refluxed for 2 hours in the presence of 1.8 ml of concentrated sulfuric acid in a reactor equipped with Dean-Stark apparatus. The water formed is removed azeotropically. The organic phase is washed three times with water and dried over sodium sulfate. This solution is filtered and the solvent is evaporated off. The product obtained distils at 147° C. under 20 hPa. 160 g (79% yield) of bis(1,3-dimethylbutyl) malonate are obtained in the form of a colorless oil, which is 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 three times with water
  4. dry with materialdried over sodium sulfate
  5. filtrationThis solution is filtered
  6. customthe solvent is evaporated off
  7. customThe product obtained
  8. customdistils at 147° C. under 20 hPa

Sources & evidence

ORD record
ord-a03c0bc6ef844325bb649436e2a4882d
Source dataset
uspto-grants-2007_05
Patent number
US07217821B2

Reaction notes

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