Isobutyraldehyde → Diethyl 2-(2-methylpropylidene)malonate

HRID 1394059Notes

Reaction equation

HRID 1394059 reaction equation
[CH3:1][CH:2]([CH3:5])[CH:3]=O.[C:6]([O:14][CH2:15][CH3:16])(=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].N1CCCCC1>C(O)(=O)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH3:5])[CH:3]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 3

HCID 6561IsobutyraldehydeHCID 7761Diethyl MalonateHCID 8082Piperidine

Product 1

HCID 348767Diethyl 2-(2-methylpropylidene)malonateYield 90.4%

Reagents, catalysts & solvents 2

HCID 243Benzoic AcidCatalystHCID 1140TolueneSolvent2×

Procedure

A mixture of 69.80 g of 2-methylpropanal, 77.30 g of diethyl malonate, 2.06 g of benzoic acid, 2.47 cm3 of piperidine and 100 cm3 of toluene is stirred at reflux for 15 hours. After cooling, 100 cm3 of toluene are added. The solution is washed in succession twice with 100 cm3 of distilled water, twice with 100 cm3 of 1M hydrochloric acid and 100 cm3 of saturated aqueous sodium carbonate solution. The organic phase is dried over anhydrous sodium sulphate and concentrated. The residue obtained is distilled under reduced pressure (117° C./10 torr) to obtain 93.44 g of the expected product in the form of a colourless oil.

Workup

  1. temperatureat reflux for 15 hours
  2. temperatureAfter cooling
  3. washThe solution is washed in succession twice with 100 cm3 of distilled water, twice with 100 cm3 of 1M hydrochloric acid and 100 cm3 of saturated aqueous sodium carbonate solution
  4. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe residue obtained
  7. distillationis distilled under reduced pressure (117° C./10 torr)

Sources & evidence

ORD record
ord-6351ff1318ad462d8e7fd32297acd6d8
Source dataset
uspto-grants-2008_03
Patent number
US07348344B2

Reaction notes

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