Pyridinium chloride → 2-(4-Hydroxyphenyl)-5-benzofurancarboxylic acid

HRID 1836059Notes

Reaction equation

HRID 1836059 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)=[CH:10][C:9]=2[CH:21]=1)=[O:4].Cl.N1C=CC=CC=1>O>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:12][C:8]3[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:21][C:9]=3[CH:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 23517377HCID 23517377, compound

Product 1

HCID 222216192-(4-Hydroxyphenyl)-5-benzofurancarboxylic acidYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 142 (0.45 g, 1.6 mmol) and Pyridine HCl (10 g) was heated to 200° C. After 1 hr, the reaction was cooled and diluted with water. The aqueous layer was extracted with EtOAc, dried, concentrated to give a solid which was triturated with CH2Cl2 and filtered to give 143 (0.23 g, 58%): Mp>300° C.; 1H NMR (DMSO-d6) δ 12.87 (br s, 1 H), 9.86 (br s, 1 H), 8.21 (d, 1 H, J=1.6 Hz), 7.86 (dd, 1 H, J=8.8 Hz, 1.5 Hz), 7.76 (d, 2H, J=8.8 Hz), 7.67 (d, 1 H, J=8.8 Hz), 7.29 (s, 1 H), 6.89 (dd, 2 H, J=7.7 Hz, 2.0 Hz); MS 253 (M−H)−

Workup

  1. temperaturethe reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas triturated with CH2Cl2
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9418492b44194f0eb3437aa409e859d9
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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