Hydrogen iodide → HCID 20256905, compound

HRID 485406Notes

Reaction equation

HRID 485406 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.I>C(O)(=O)C.[Cl-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24841Hydrogen iodideHCID 54151673HCID 54151673, compound

Product 1

HCID 20256905HCID 20256905, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5234Sodium ChlorideSolvent

Procedure

A solution of 4-(4-bromophenyl)-4-phenylbut-3-enoic acid (5.0 g., 0.0157 mole) in glacial acetic acid (50 ml.) was treated with 56.9% aqueous hydriodic acid (22.5 ml.) and red phosphorus (4.5 g.) and the resulting mixture stirred at reflux for 16 hours. The reaction mixture was then cooled to room temperature, diluted with saturated aqueous sodium chloride solution (250 ml.) and extracted with methylene chloride (250 ml.). The extract was washed with saturated aqueous sodium chloride solution (2×100 ml.), dried (MgSO4) and evaporated under vacuum to the desired butanoic acid derivative, which was used in the next step without further purification (5 g., oil, ca. 99% yield).

Workup

  1. temperatureat reflux for 16 hours
  2. extractionextracted with methylene chloride (250 ml.)
  3. washThe extract was washed with saturated aqueous sodium chloride solution (2×100 ml.)
  4. dry with materialdried (MgSO4)
  5. customevaporated under vacuum to the desired butanoic acid derivative, which
  6. customwas used in the next step without further purification (5 g., oil, ca. 99% yield)

Sources & evidence

ORD record
ord-78b962dcfcac4254a9a685f635fc1eae
Source dataset
uspto-grants-1985_08
Patent number
US04536518

Reaction notes

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