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

HRID 1836046Notes

Reaction equation

HRID 1836046 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>CCOC(C)=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

5

Reactant 3

HCID 962WaterHCID 10176127Pyridinium chlorideHCID 10236364HCID 10236364, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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 exracted with EtOAc. The EtOAc layer was dried over MgSO4, concentrated and the product was purified by column chrmatography 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, 1H, 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. dry with materialThe EtOAc layer was dried over MgSO4
  3. concentrationconcentrated
  4. customthe product was purified by column chrmatography on silica gel (75% EtOAc/hex)

Sources & evidence

ORD record
ord-7dbcaf32191b4c37b4485c1262e576b6
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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