5-Phenyl-2-benzofurancarboxylic acid → HCID 20329640, compound

HRID 1395679Notes

Reaction equation

HRID 1395679 reaction equation
[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:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Na].[Hg].[OH-].[Na+]>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][C:11]=3[CH:18]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 129909085-Phenyl-2-benzofurancarboxylic acid

Product 1

HCID 20329640HCID 20329640, compound

Reagents, catalysts & solvents 2

HCID 9837419Sodium amalgamCatalystHCID 14798Sodium HydroxideSolvent

Procedure

5.0 g of 1C was mixed with 90 ml of 10% sodium hydroxide solution. Sodium amalgam (prepared from 1.5 g of sodium and 50 g of mercury) was added to the stirred mixture over a period of one hour. The mixture was then stirred for 24 hours and allowed to stand at room temperature for an additional 24 hours. The mercury was separated, the solution was neutralized with dilute hydrochloric acid and extracted with ether. The extract was dried (Na2SO4) and concentrated under reduced pressure. The residue was recrystallized from ethanol to give 2,3-dihydro-5-phenyl-2-benzofurancarboxylic acid (1D), as white crystals, mp: 186°-187° C.

Workup

  1. waitto stand at room temperature for an additional 24 hours
  2. customThe mercury was separated
  3. extractionextracted with ether
  4. dry with materialThe extract was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-dba68c2154b34ea0b2f6dad72872b702
Source dataset
uspto-grants-1980_05
Patent number
US04205080

Reaction notes

Loading…