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

HRID 2211696Notes

Reaction equation

HRID 2211696 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)C=O>[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% dispersion in liquid paraffin, 5.92 g, 148 mmol) in N,N-dimethylformamide (150 ml) was added at 0° C. triethyl 2-phosphonopropionate (35.0 g, 148 mmol) and the resulting 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 resulting mixture was stirred at room temperature for 30 minutes. Water was added into the reaction solution and the product was extracted twice with ethyl acetate. The combined extracts were washed with water, dried on magnesium sulfate, and then concentrated under reduced pressure to obtain 30.1 g (96% yield) of the oily title compound.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 30 minutes
  2. extractionthe product was extracted twice with ethyl acetate
  3. washThe combined extracts were washed with water
  4. customdried on magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-adb4994a208e4577b6c7f9e818ce384a
Source dataset
uspto-grants-2006_09
Patent number
US07101867B2

Reaction notes

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