Potassium Iodide → HCID 67145241, compound

HRID 630382Notes

Reaction equation

HRID 630382 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O>[Br:12][CH2:13][CH2:14][CH2:15][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([CH3:10])=[O:11])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 70192744-Hydroxyphenylacetone

Product 1

HCID 67145241HCID 67145241, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-hydroxyphenyl)propan-2-one (2.2 g, 0.01 mol) in dimethylformamide (10 mL) was added 1,3-dibromopropane (7.6 mL, 0.07 mol), potassium carbonate (2.3 g, 0.01 mol) and potassium iodide (0.7 g, 0.004 mol). The mixture was stirred at room temperature for 72 hours. Water was added into the reaction vessel and the crude was extracted with ethyl acetate. The organic layer was washed with water and brine, dried, filtered and evaporated to dryness. The crude obtained was purified by column chromatography with silica gel, eluting with hexane/ethyl acetate (from 100% to 10%), obtaining the title compound (54%).

Workup

  1. extractionthe crude was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude obtained
  7. customwas purified by column chromatography with silica gel
  8. washeluting with hexane/ethyl acetate (from 100% to 10%)

Sources & evidence

ORD record
ord-77bf390012ed44a59b0fabd4d3b7a7fd
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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