Dimethyl Sulfate → Methyl 3-(4-formylphenyl)-2-propenoate

HRID 2227491Notes

Reaction equation

HRID 2227491 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1)=[O:2].S(OC)(O[CH3:18])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([CH:7]=[CH:8][C:9]([O:11][CH3:18])=[O:10])=[CH:5][CH:4]=1)=[O:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 980772-Propenoic acid, 3-(4-formylphenyl)-

Product 1

HCID 53401287Methyl 3-(4-formylphenyl)-2-propenoateYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-formylcinnamic acid (10.0 g), dimethyl sulfate (5.9 ml) and potassium carbonate (11.8 g) in 100 ml dimethylformamide was stirred at room temperature for 17 hours. After removal of inorganic salts by filtration, saturated aqueous sodium bicarbonate was added to the reaction mixture, which was then extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate and brine, and dried over sodium sulfate. The drying agent was filtered off and the filtrate was evaporated and dried under reduced pressure to give methyl 4-formylcinnamate (9.78 g, 91%) as a pale yellow solid.

Workup

  1. customAfter removal of inorganic salts
  2. filtrationby filtration, saturated aqueous sodium bicarbonate
  3. additionwas added to the reaction mixture, which
  4. extractionwas then extracted twice with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationThe drying agent was filtered off
  8. customthe filtrate was evaporated
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-abcb9963874b4695ad450c140c07fb61
Source dataset
uspto-grants-2002_07
Patent number
US06413995B1

Reaction notes

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