Aniline → 2-Phenylfuran

HRID 1722440Notes

Reaction equation

HRID 1722440 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1>>[C:2]1([C:9]2[O:8][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 8029Furan

Product 1

HCID 5193632-PhenylfuranYield 39%

Procedure

A solution of aniline (12.5 g, 0.134M) and i-amylnitrite (27.5 ml, 0.205M) in furan (400 ml) was stirred at 30° C. (bath temperature) for 24 hours under N2. The mixture was then washed with water and saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated. The brown residue was fitered through a short column of neutral alumina (activity grade II) using pentane as an eluent. The fractions were combined and concentrated and the residue distilled in vacuo to give pure 2-phenylfuran (7.65 g, 39% yield), bp 51°-54° C. (1.0 mm). NMR (CDCl3) δ6.45 ppm (dd, 1H, J=1.5, 3.0 Hz, furan-H4), 6.62 (d, 1H, J=4.0 Hz, furan-H3), 7.2-7.8 (m, 6H, phenyl and furan-H5).

Workup

  1. washThe mixture was then washed with water and saturated NaCl solution
  2. dry with materialdried over anhydrous Na2SO4
  3. customevaporated
  4. concentrationconcentrated
  5. distillationthe residue distilled in vacuo

Sources & evidence

ORD record
ord-50d9a950e7fc4e95bd4dd87b4952b327
Source dataset
uspto-grants-1989_08
Patent number
US04855426

Reaction notes

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