Cuminaldehyde → Ethyl 3-(4-isopropylphenyl)-2-methyl-2-propenoate

HRID 1787119Notes

Reaction equation

HRID 1787119 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[CH:18]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1)([CH3:20])[CH3:19].O>CN(C=O)C>[CH:18]([C:21]1[CH:28]=[CH:27][C:24]([CH:25]=[C:8]([CH3:9])[C:6]([O:5][CH2:4][CH3:3])=[O:7])=[CH:23][CH:22]=1)([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 326CuminaldehydeHCID 962WaterHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionate

Product 1

HCID 68704703Ethyl 3-(4-isopropylphenyl)-2-methyl-2-propenoateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (a 60% liquid paraffin dispersion, 5.92 g, 148 mmol) in DMF (150 mL) was added triethyl 2-phosphonopropionate (35.0 g, 148 mmol) at 0° C., and the mixture was stirred at the same temperature for 10 minutes. To the reaction solution was added 4-isopropylbenzaldehyde (20.0 g, 135 mmol), and the mixture was stirred at room temperature 30 minutes. Water was added to the reaction solution, and the product was extracted twice with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and then concentrated under reduced pressure to obtain 30.1 g (yield 96%) of the oily title compound.

Workup

  1. stirringthe mixture was stirred at room temperature 30 minutes
  2. extractionthe product was extracted twice with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7399efa988b74eafa43d6ae871129c0d
Source dataset
uspto-grants-2009_03
Patent number
US07507841B2

Reaction notes

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