Iodine → HCID 20546990, compound

HRID 2059292Notes

Reaction equation

HRID 2059292 reaction equation
[OH-].[Na+].[I:3]I.[C:5]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=[CH:9][C:8]([C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)([OH:14])[C:12]#[CH:13])=[CH:7][CH:6]=1>CO>[C:5]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:10]=[CH:9][C:8]([C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)([OH:14])[C:12]#[C:13][I:3])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14798Sodium HydroxideHCID 20546969HCID 20546969, compound

Product 1

HCID 20546990HCID 20546990, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40 ml of concentrated sodium hydroxide solution and 25.4 g (0.1 mol) of iodine were simultaneously introduced into a solution of 31.9 g (0.1 mol) of 3-(4-biphenylyl)-3-(3-chlorophenyl)-1-propyn-3-ol in 350 ml of methanol at 20° C., with slight external cooling and while stirring. The mixture was stirred for three hours and filtered to remove a slight turbidity and the filtrate was stirred into 1,000 ml of water. The reaction product thereby separated out as a semi-solid mass. The supernatant liquid was decanted, the residue was taken up in ethyl acetate and the solution was washed several times with 100 ml of water each time and dried over sodium sulphate. Thereafter, it was concentrated by distilling off the solvent in vacuo, and the oily residue was dissolved in a little ether. After adding petroleum ether, crystallization occurred. 25.3 g (56.9% of theory) of 3-(4-biphenylyl)-3-(3-chlorophenyl)-1-iodo-1-propyn-3-ol were obtained as colorless crystals of melting point 99°-100° C.

Workup

  1. temperaturewith slight external cooling
  2. stirringThe mixture was stirred for three hours
  3. filtrationfiltered
  4. customto remove a slight turbidity
  5. stirringthe filtrate was stirred into 1,000 ml of water
  6. customThe reaction product thereby separated out as a semi-solid mass
  7. customThe supernatant liquid was decanted
  8. washthe solution was washed several times with 100 ml of water each time
  9. dry with materialdried over sodium sulphate
  10. concentrationThereafter, it was concentrated
  11. distillationby distilling off the solvent in vacuo
  12. dissolutionthe oily residue was dissolved in a little ether
  13. additionAfter adding
  14. custompetroleum ether, crystallization

Sources & evidence

ORD record
ord-303b5ece8a074c1bb891d2de5bcb4f27
Source dataset
uspto-grants-1982_03
Patent number
US04322442

Reaction notes

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