Acetonitrile → Ethyl 1,3-benzodioxole-5-propionate

HRID 1445304Notes

Reaction equation

HRID 1445304 reaction equation
[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=2[O:2]1.[H][H].P([O-])([O-])([O-])=O.P([O-])(O)(O)=O.[K+].[C:28](#N)[CH3:29]>C(O)C.[Pd]>[CH2:28]([O:9][C:8](=[O:10])[CH2:7][CH2:6][C:5]1[CH:11]=[CH:12][C:13]2[O:14][CH2:1][O:2][C:3]=2[CH:4]=1)[CH3:29]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acidHCID 86606725HCID 86606725, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 81545Ethyl 1,3-benzodioxole-5-propionate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

First, 50 g of 3,4-methylenedioxy cinnamic acid was dissolved in 500 ml of ethanol. To the mixture, 5 g of 5% Pd/C catalyst was added. The reaction system was replaced with hydrogen gas and stirred at 25° C. for 6 hours. After completion of the reaction, the Pd/C catalyst was removed by filtration. The resultant ethanol solution was cooled to 5° C. and 37.1 g of thionyl chloride was added dropwise for one hour. After completion of the dropwise addition, the ethanol solution was stirred for a further 3 hours with keeping the inner temperature at 5° C. After completion of the reaction, a solvent was distilled off under reduced pressure to obtain 54.7 g of an orange concentrate. A part of the concentrate was taken and analyzed by high performance column chromatography (HPLC) (column: LiChrosphere 100 PR-8(E), 250 mm×4.0 mm I.D., manufactured by Merck Ltd., mobile phase: an aqueous solution of phosphate/potassium dihydrogenphosphate: acetonitrile=1:1, flow rate: 1 ml/minute, detection wavelength: 210 nm, column temperature: 30° C.). As a result, it was observed that 49.8 g of the titled compound was obtained.

Workup

  1. customAfter completion of the reaction
  2. customthe Pd/C catalyst was removed by filtration
  3. temperatureThe resultant ethanol solution was cooled to 5° C.
  4. addition37.1 g of thionyl chloride was added dropwise for one hour
  5. additionAfter completion of the dropwise addition
  6. stirringthe ethanol solution was stirred for a further 3 hours
  7. customat 5° C
  8. customAfter completion of the reaction
  9. distillationa solvent was distilled off under reduced pressure
  10. customto obtain 54.7 g of an orange concentrate
  11. custom30° C.

Sources & evidence

ORD record
ord-81cc3af5f968473f8813e9a17f7108ff
Source dataset
uspto-grants-2010_02
Patent number
US07666659B2

Reaction notes

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