Potassium Iodide → HCID 250147, compound

HRID 1461862Notes

Reaction equation

HRID 1461862 reaction equation
[C].[K].[I-].[K+].[CH2:5]([O:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH2:6][CH2:7][CH3:8].[CH2:21](Cl)[C:22](=[CH2:24])[CH3:23]>CN(C)C=O>[CH2:5]([O:9][C:10](=[O:20])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:23][C:22]([CH3:24])=[CH2:21])=[CH:15][CH:14]=1)[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 112413-Chloro-2-methyl-1-propeneHCID 54465584Butyl 3-(4-hydroxyphenyl)prop-2-enoateHCID 178477806HCID 178477806, compound

Product 1

HCID 250147HCID 250147, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

121 g (0.88M) of finely powdered potassium carbon are are introduced into 400 m N,N-dimethyl formamide. With stirring lg of potassium iodide, 176 g (0.8M) of p-hydroxy cinnamic acid n-butylester (see above) and 85 m (0.87M) of methallyl chloride are added. Under a blanket of nitrogen and with stirring the mixture is heated up to 70° C. and kept at that temperature until the starting material is consumed (about 21 hours). The mixture is cooled to room temperature and 500 m of water are added. The solution is extracted three times with a total of 1.2 liter of hexane and the hexane extracts are subsequently washed with a 10% solution of sodium carbonate and water. The hexane extract is evaporated at 30° C. in vacuo (about 12 mbar) to dryness. The residue is crystallised from 80 m of methanol at 0° C. The colourless crystalline product is collected by filtration and dried in high vacuo (about 0.1 mbar) at room temperature. 163.5 g (74.5% of theory) of product melting at 32°-33° C. are obtained.

Workup

  1. additionare added
  2. customis consumed (about 21 hours)
  3. temperatureThe mixture is cooled to room temperature
  4. addition500 m of water are added
  5. extractionThe solution is extracted three times with a total of 1.2 liter of hexane
  6. washthe hexane extracts are subsequently washed with a 10% solution of sodium carbonate and water
  7. extractionThe hexane extract
  8. customis evaporated at 30° C. in vacuo (about 12 mbar) to dryness
  9. customThe residue is crystallised from 80 m of methanol at 0° C
  10. filtrationThe colourless crystalline product is collected by filtration
  11. customdried in high vacuo (about 0.1 mbar) at room temperature

Sources & evidence

ORD record
ord-e577790f956441a29f37c762ee9c6d54
Source dataset
uspto-grants-1991_12
Patent number
US05077422

Reaction notes

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