Iodine → HCID 13101194, compound

HRID 2417737Notes

Reaction equation

HRID 2417737 reaction equation
[OH-].[Na+].[F:3][C:4]([F:18])([F:17])[O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([OH:16])([CH3:15])[C:13]#[CH:14])=[CH:8][CH:7]=1.[I:19]I.O>CO>[I:19][C:14]#[C:13][C:12]([C:9]1[CH:8]=[CH:7][C:6]([O:5][C:4]([F:17])([F:18])[F:3])=[CH:11][CH:10]=1)([OH:16])[CH3:15]

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 14798Sodium HydroxideHCID 13101193HCID 13101193, compound

Product 1

HCID 13101194HCID 13101194, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

40 ml of concentrated sodium hydroxide solution were added dropwise to a solution of 23 g (0.1 mol) of 3-(4-trifluoromethoxyphenyl)-but-1-yn-3-ol in 250 ml of methanol at 15°-20° C. in the course of 30 minutes, while stirring, and 25.4 g (0.1 mol) of iodine were simultaneously introduced in portions. After three hours, the reaction mixture was stirred into 1,000 ml of water. The initially oil reaction product crystallized on standing. The solid material was taken up in 200 ml of ethyl acetate, the solution was washed twice with 100 ml of water, and the organic phase was dried over anhydrous sodium sulphate and concentrated by evaporation under reduced pressure. The residual oil was dissolved in a small quantity of petroleum ether, the solution was cooled and the precipitated crystals were filtered off under suction. 17.2 g (=48.2% of theory) of colorless crystals of melting point 75°-76° C. were obtained.

Workup

  1. customThe initially oil reaction product
  2. customcrystallized
  3. washthe solution was washed twice with 100 ml of water
  4. dry with materialthe organic phase was dried over anhydrous sodium sulphate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. dissolutionThe residual oil was dissolved in a small quantity of petroleum ether
  7. temperaturethe solution was cooled
  8. filtrationthe precipitated crystals were filtered off under suction
  9. custom17.2 g (=48.2% of theory) of colorless crystals of melting point 75°-76° C. were obtained

Sources & evidence

ORD record
ord-905e7a15d66a488489a4cc60de844771
Source dataset
uspto-grants-1984_09
Patent number
US04469902

Reaction notes

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