Ethanol → HCID 20333807, compound

HRID 262212Notes

Reaction equation

HRID 262212 reaction equation
C(C1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[C:15]([CH2:18][C:19]([O:21]C)=[O:20])[CH:16]=[CH:17][C:12]=3[O:11][CH:10]=2)=[CH:5][CH:4]=1)#N.[CH2:23]([OH:25])[CH3:24].[OH-:26].[Na+]>O>[C:23]([C:24]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[C:15]([CH2:18][C:19]([OH:21])=[O:20])[CH:16]=[CH:17][C:12]=3[O:11][CH:10]=2)=[CH:5][CH:4]=1)([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 54420298HCID 54420298, compound

Product 1

HCID 20333807HCID 20333807, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 5 g. of the product of step A in 20 ml. of ethanol is added 50 ml. of 30 percent sodium hydroxide solution, and the mixture is refluxed for 30 minutes, 75 ml. of water is added, and the mixture is refluxed for an additional three hours. The mixture is decanted into 125 ml. of 6N hydrochloric acid, the solid is separated by filtration then recrystallized from acetic acid to provide 3-(4-carboxyphenyl)benzofuran-5-acetic acid, m.p. 278°-281° C.

Workup

  1. additionTo a suspension of 5 g
  2. temperaturethe mixture is refluxed for an additional three hours
  3. customThe mixture is decanted into 125 ml
  4. customof 6N hydrochloric acid, the solid is separated by filtration
  5. customthen recrystallized from acetic acid

Sources & evidence

ORD record
ord-1e940be1b38e49a1a706254c55283ce1
Source dataset
uspto-grants-1979_05
Patent number
US04153716

Reaction notes

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