Potassium Iodide → HCID 250147, compound

HRID 1165982Notes

Reaction equation

HRID 1165982 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 ml N,N-dimethyl formamide. With stirring 1 g of potassium iodide, 176 g (0.8M) of p-hydroxy cinnamic acid n-butylester (see above) and 85 ml (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 ml 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 ml 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 ml 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 ml 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-311e7eb79f42444b8412e9011467fc8f
Source dataset
uspto-grants-1990_03
Patent number
US04912241

Reaction notes

Loading…