Ethyl 5-phenylbenzofuran-2-carboxylate → 5-Phenyl-2-benzofurancarboxylic acid

HRID 2057959Notes

Reaction equation

HRID 2057959 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15]([O:17]CC)=[O:16])=[CH:12][C:11]=3[CH:20]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[OH-].[K+]>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][C:11]=3[CH:20]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 20329644Ethyl 5-phenylbenzofuran-2-carboxylate

Product 1

HCID 129909085-Phenyl-2-benzofurancarboxylic acid

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A mixture of 1.3 g of 10B and 50 ml of 10% alcoholic potassium hydroxide was refluxed for 4 hours. The solvent was evaporated under reduced pressure and the residue was washed with ether and dissolved in water. The basic solution was acidified with dilute hydrochloric acid and extracted with ether. The ether layer was extracted with dilute sodium bicarbonate solution. The aqueous extract was acidified with dilute hydrochloric acid and extracted with ether. The ether extract was dried (Na2SO4), concentrated under reduced pressure, and the resulting residue was crystallized from ethanol to give 5-phenyl-2-benzofurancarboxylic acid (10C), as white solid, mp: 220°-221° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe solvent was evaporated under reduced pressure
  3. washthe residue was washed with ether
  4. dissolutiondissolved in water
  5. extractionextracted with ether
  6. extractionThe ether layer was extracted with dilute sodium bicarbonate solution
  7. extractionThe aqueous extract
  8. extractionextracted with ether
  9. extractionThe ether extract
  10. dry with materialwas dried (Na2SO4)
  11. concentrationconcentrated under reduced pressure
  12. customthe resulting residue was crystallized from ethanol

Sources & evidence

ORD record
ord-2c101d7615114511ac7ac03b78206a26
Source dataset
uspto-grants-1980_07
Patent number
US04213999

Reaction notes

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