Potassium Carbonate → 2-(1,3-Dioxaindan-5-yl)propanoic acid

HRID 1657884Notes

Reaction equation

HRID 1657884 reaction equation
[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH:6]=[CH:7]C(O)=O)=[CH:4][C:3]=2[O:2]1.[C:15](=O)([O-:17])[O-:16].[K+].[K+].[H][H]>[Pd]>[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH:6]([CH3:7])[C:15]([OH:17])=[O:16])=[CH:4][C:3]=2[O:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acidHCID 178418361HCID 178418361, compound2×

Product 1

HCID 183996542-(1,3-Dioxaindan-5-yl)propanoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 50 g. of 3,4-methylenedioxycinnamic acid in 200 ml. of a 2 N potassium carbonate solution in a Parr shaker was added 0.5 g. of a five percent palladium on carbon catalyst. Hydrogen was introduced into the reactor to a pressure of 30 psig. The reaction was allowed to proceed until 0.26 moles of hydrogen were taken up (about 4 hours). At the completion of the reaction the mixture was filtered to remove the catalyst. Acidification of the mixture resulted in the precipitation of the desired 3,4-methylenedioxyphenylpropionic acid in 95 percent yield.

Workup

  1. custom(about 4 hours)
  2. customAt the completion of the reaction the mixture
  3. filtrationwas filtered
  4. customto remove the catalyst

Sources & evidence

ORD record
ord-2a231f45f5604169928af31b46407784
Source dataset
uspto-grants-1976_06
Patent number
US03962282

Reaction notes

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