Pyridinium chloride → 4-(5-Hydroxy-benzofuran-2-yl)-benzoic acid

HRID 1794542Notes

Reaction equation

HRID 1794542 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][C:13]=3[CH:14]=2)=[CH:6][CH:5]=1.Cl.N1C=CC=CC=1>O>[OH:19][C:16]1[CH:17]=[CH:18][C:12]2[O:11][C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][CH:6]=3)=[CH:14][C:13]=2[CH:15]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 10236364HCID 10236364, compound

Product 1

HCID 101492294-(5-Hydroxy-benzofuran-2-yl)-benzoic acidYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-(5-Methoxy-benzofuran-2-yl)-benzoic acid methyl ester (0.5 g, 1.8 mmol) and Pyridine HCl (5 g) was heated to 200° C. After 2 hr, the reaction was cooled and poured into water and extracted with EtOAc. The EtOAc layer was dried over MgSO4, concentrated and the product was purified by column chromatography on silica gel (75% EtOAc/hex) to give a solid (0.21 g, 47%): 1H NMR (DMSO-d6) δ 13.07 (br s, 1 H), 9.29 (br s, 1 H), 8.02 (d, 2 H, J=8.1 Hz), 7.97 (d, 2 H, J=8.7 Hz), 7.46 (m, 2 H), 6.97 (d, 1 H, J=2.9 Hz), 6.79 (dd, 1 H, J=9.3 Hz, 2.9 Hz); MS 253 (M−H)−

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with EtOAc
  3. dry with materialThe EtOAc layer was dried over MgSO4
  4. concentrationconcentrated
  5. customthe product was purified by column chromatography on silica gel (75% EtOAc/hex)

Sources & evidence

ORD record
ord-c8260470879d4fa987f88f9cf2ce0088
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

Loading…