Acetic Acid → HCID 22761739, compound

HRID 1834044Notes

Reaction equation

HRID 1834044 reaction equation
C(C1[CH:17]=[CH:16][C:6]2[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][O:9][C:5]=2[CH:4]=1)#N.[C:18]([OH:21])(=[O:20])[CH3:19].Cl>O>[C:10]1([C:7]2[C:6]3[CH:16]=[CH:17][C:19]([C:18]([OH:21])=[O:20])=[CH:4][C:5]=3[O:9][CH:8]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric Acid2×HCID 22761737HCID 22761737, compound

Product 1

HCID 22761739HCID 22761739, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 54.7 g of 6-cyano-3-phenylbenzofuran, 200 ml of acetic acid and 100 ml of hydrochloric acid is heated to its reflux temperature and maintained at reflux for about 20 hours. An additional 100 ml of hydrochloric acid is added and the mixture is refluxed further for about 27 hours. The reaction mixture is then added to water and the aqueous solution is extracted with diethyl ether. The ether layer is extracted with dilute sodium hydroxide solution. The basic aqueous solution is acidified with 6N hydrochloric acid and the solid precipitate is collected by filtration. The solid is recrystallized from aqueous ethanol to provide 3-phenyl-6-benzofurancarboxylic acid, m.p. 160°-170° C.

Workup

  1. temperatureis heated to its
  2. temperaturereflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for about 20 hours
  5. temperaturethe mixture is refluxed further for about 27 hours
  6. extractionthe aqueous solution is extracted with diethyl ether
  7. extractionThe ether layer is extracted with dilute sodium hydroxide solution
  8. filtrationthe solid precipitate is collected by filtration
  9. customThe solid is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-71612c380864413cb7fc4c649178f8dc
Source dataset
uspto-grants-1978_01
Patent number
US04067993

Reaction notes

Loading…