1-Benzofuran-4-carboxylic acid → 2,3-Dihydro-1-benzofuran-4-carboxylic acid

HRID 1602428Notes

Reaction equation

HRID 1602428 reaction equation
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[C:4]2[CH:3]=[CH:2]1>C(O)(=O)C.[Pd]>[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[C:4]2[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 223241171-Benzofuran-4-carboxylic acid

Product 1

HCID 187874442,3-Dihydro-1-benzofuran-4-carboxylic acidYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Benzofuran-4-carboxylic acid (10.0 g, 61.7 mmol) was hydrogenated (60 psi) in acetic acid (100 mL) over 10% Pd/C (2 g) for 12 hr. The mixture was filtered and the filtrate was diluted with water (500 mL) to give 2,3-dihydrobenzofuran-4-carboxylic acid as a white powder (8.4 g, 83%). A sample was recrystallized from isopropanol to give fine white needles (mp: 185.5-187.5° C).

Workup

  1. customfor 12 hr
  2. filtrationThe mixture was filtered
  3. additionthe filtrate was diluted with water (500 mL)

Sources & evidence

ORD record
ord-eed91001ee6a492fa058a20411d0cd2d
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

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