Water → Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoate

HRID 2211697Notes

Reaction equation

HRID 2211697 reaction equation
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[CH3:9])=[O:7].[CH3:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.O>CN(C)C=O>[CH3:9][C:8](=[CH:23][C:22]1[CH:25]=[CH:26][C:19]([CH3:18])=[CH:20][CH:21]=1)[C:6]([O:5][CH2:4][CH3:3])=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 24758Sodium hydrideHCID 107155Triethyl 2-phosphonopropionate

Product 1

HCID 68712312Ethyl 2-methyl-3-(4-methylphenyl)-2-propenoateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (a 60% dispersion in liquid paraffin, 15.0 g, 375 mmol) in N,N-dimethylformamide (160 ml) was added at 0° C. a solution of triethyl 2-phosphonopropionate (87.7 g, 368 mmol) in N,N-dimethylformamide (10 ml) and the resulting mixture was stirred at the same temperature for 1 hour. To the reaction solution was added 4-methylbenzaldehyde (43.3 g, 361 mmol) and the resulting mixture was stirred at room temperature for 1 hour. 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 66.7 g (91% yield) of the oily title compound.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 1 hour
  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-3639eb7d53bf48209d262eadb940099a
Source dataset
uspto-grants-2006_09
Patent number
US07101867B2

Reaction notes

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