Ethanol → HCID 70609418, compound

HRID 597287Notes

Reaction equation

HRID 597287 reaction equation
[OH-:1].[Na+].[Br:3][C:4]1[O:5][C:6]2[C:18](CC#N)=[CH:17][CH:16]=[CH:15][C:7]=2[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:22]([OH:24])[CH3:23]>>[Br:3][C:4]1([CH2:23][C:22]([OH:1])=[O:24])[CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[C:15]2[CH:16]=[CH:17][CH:18]=[C:6]2[O:5]1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 21447346HCID 21447346, compound

Product 1

HCID 70609418HCID 70609418, compound

Procedure

To a mixture of 50% sodium hydroxide solution (35 ml.) and ethanol (100 ml.) is added 2-bromo-7-cyanomethyl-3-phenylbenzofuran (10 g., 0.032 mole). The mixture is heated to reflux temperature and maintained at reflux for about sixteen hours, then concentrated in vacuo. The residue is diluted with water, then extracted (washed) with diethyl ether. The aqueous layer is acidified with hydrochloric acid, yielding a precipitate which is collected by filtration and recrystallized twice from benzene-hexane mixtures to give 2-bromo-3-phenyl-7-benzofuranacetic acid, m.p. 162°-163.5° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature
  3. temperaturemaintained
  4. temperatureat reflux for about sixteen hours
  5. concentrationconcentrated in vacuo
  6. additionThe residue is diluted with water
  7. extractionextracted
  8. wash(washed) with diethyl ether
  9. customyielding a precipitate which
  10. filtrationis collected by filtration
  11. customrecrystallized twice from benzene-hexane mixtures

Sources & evidence

ORD record
ord-0238ca1b6857413184c609d1d6117288
Source dataset
uspto-grants-1977_03
Patent number
US04013692

Reaction notes

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