4-Benzofuranol → 2,3-dihydrobenzofuran-4-ol

HRID 1699131Notes

Reaction equation

HRID 1699131 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)(=O)C.[Pd]>[OH:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 116079214-BenzofuranolHCID 178418361HCID 178418361, compound2×

Product 1

HCID 112288352,3-dihydrobenzofuran-4-olYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

At ambient temperature a rapidly stirred solution of 4-hydroxybenzofuran (2.0 g) (prepared by the method of G. Keen & P. Maddocks Syn. Comm., 16(13), 1635-1640 (1986)) in glacial acetic acid (30 ml) containing 30% palladium on carbon (0.2 g) was exposed to an atmosphere of hydrogen. When uptake of hydrogen had ceased the solution was filtered and the filter cake washed with glacial acetic acid. The combined filtrates were evaporated to dryness to give of 4-hydroxy-dihyrobenzofuran (2.05 g) 1H NMR (DMSO-d6, 300 MHz, ppm): 3.0(2H,t), 4.5(2H,t), 6.2(1H.d), 6.3(1H,d), 6.8(1H,t), 9.5(1H,b) m/Z 135 (M−H).

Workup

  1. filtrationwas filtered
  2. washthe filter cake washed with glacial acetic acid
  3. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-11b53b450190442185c5aed692ed793e
Source dataset
uspto-grants-2002_02
Patent number
US06344570B1

Reaction notes

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