Water → 3-(Benzodioxol-5-yl)propionic acid

HRID 5025

Reaction equation

HRID 5025 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.O.[H][H]>[OH-].[Na+].[Pd]>[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 648103-(Benzodioxol-5-yl)propionic acidYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 10.0 g of 3,4-methylenedioxycinnamic acid dissolved in 130 ml of 10% NaOH and 80 ml of distilled water was added 1.0 g of 5% Pd-C. This mixture was reacted at 40 psi until the consumption of hydrogen gas was ceased and then filtered through a Celite layer. The filtrate was acidified with concentrated hydrochloric acid, allowed to be cooled and filtered to give solids. The obtained solids were washed twice with 100 ml of cold water and dried to provide 9.8 g(yield 97%) of 3-(3,4-methylenedioxyphenyl) propanoic acid, having the characteristics of: NMR(CDCl3, 200 MHz) δ2.62(t, J=7 Hz, 2H, CH2), 2.88(t, J=7 Hz, 2H, CH2N), 5.93(s, 2H, CH2O2), 6.63-6.76(s, 3H, ArH).

Workup

  1. filtrationfiltered through a Celite layer
  2. temperatureto be cooled
  3. filtrationfiltered
  4. customto give solids
  5. washThe obtained solids were washed twice with 100 ml of cold water
  6. customdried

Sources & evidence

ORD record
ord-cba18c7783e64b07b2d8f20d24a2f6f6
Source dataset
uspto-grants-1993_09
Patent number
US05242944

Linked notes

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