HCID 29938143, compound → Acetic Acid

HRID 420899Notes

Reaction equation

HRID 420899 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[H][H]>C(O)(=O)C.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[C:12]([OH:14])(=[O:13])[CH3:11]

Participants

6

Reactant 2

HCID 29938143HCID 29938143, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 176Acetic AcidYield 8,348.1%HCID 11053175Ethyl 3-(2,3-dihydrobenzofuran-5-yl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Ethyl (E)-3-(2,3-dihydrobenzofuran-5-yl)propenoate (50.0 g, 227 mmol) was dissolved in acetic acid (312 g), and the reaction system was replaced with nitrogen. Then, 5% Pd/C (4.96 g, as dry weight) was added to the solution and pressurized with hydrogen to 196 to 294 kPa. The mixture was reacted at 50° C. for 1 hr under a pressure of 196 to 294 kPa. The catalyst was filtered, and washed with acetic acid (208 g) to give a solution of the title compound in acetic acid (amount 569 g, apparent yield 100%).

Workup

  1. customThe mixture was reacted at 50° C. for 1 hr under a pressure of 196 to 294 kPa
  2. filtrationThe catalyst was filtered
  3. washwashed with acetic acid (208 g)

Sources & evidence

ORD record
ord-693d494932d3468e8c92c59aba079547
Source dataset
uspto-grants-2012_01
Patent number
US08097737B2

Reaction notes

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