Ethanol → HCID 70608902, compound

HRID 597285Notes

Reaction equation

HRID 597285 reaction equation
[OH-:1].[K+].C(C[C:6]1[C:14]2[O:13][CH:12]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)#N.[CH2:22]([OH:24])[CH3:23]>>[F:21][C:18]1[CH:17]=[CH:16][C:15]([C:11]2[CH:10]=[C:9]3[CH:8]=[CH:7][CH:6]=[C:14]3[O:13][C:12]=2[CH2:23][C:22]([OH:1])=[O:24])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 21447365HCID 21447365, compound

Product 1

HCID 70608902HCID 70608902, compound

Procedure

Potassium hydroxide (85%, 49 g.), 7-cyanomethyl-3-(4-fluorophenyl)benzofuran (48.8 g., 0.194 mole) and 95% ethanol (500 ml.) are mixed and heated at reflux temperature overnight under a nitrogen atmosphere. The mixture is then concentrated by evaporation in vacuo, diluted with water and extracted with diethyl ether. The aqueous phase is filtered, then acidified by the slow addition of hydrochloric acid. The solid is collected by filtration and recrystallized from aqueous ethanol (65%) with treatment with decolorizing charcoal, giving yellow crystals. Another recrystallization from an ethanol-petroleum ether mixture (about 5:1) gives yellow crystals of 3-(4 -fluorophenyl)-7-benzofuranacetic acid, m.p. 169°-170° C.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature overnight under a nitrogen atmosphere
  3. concentrationThe mixture is then concentrated by evaporation in vacuo
  4. additiondiluted with water
  5. extractionextracted with diethyl ether
  6. filtrationThe aqueous phase is filtered
  7. additionacidified by the slow addition of hydrochloric acid
  8. filtrationThe solid is collected by filtration
  9. customrecrystallized from aqueous ethanol (65%) with treatment with decolorizing charcoal
  10. customgiving yellow crystals
  11. customAnother recrystallization from an ethanol-petroleum ether mixture (about 5:1)

Sources & evidence

ORD record
ord-9c4aa895c2104b278b5acc2273ecb3ed
Source dataset
uspto-grants-1977_03
Patent number
US04013692

Reaction notes

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