Potassium Iodide → 1-[4-(3-Carbomethoxyprop-2-eneoxy)phenyl]propan-2-one

HRID 1758987

Reaction equation

HRID 1758987 reaction equation
C1[O:14][C:4]([CH3:13])([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)OC1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22]/[CH:23]=[CH:24]/[C:25]([O:27][CH3:28])=[O:26].[I-].[K+]>CC(C)=O>[C:25]([CH:24]=[CH:23][CH2:22][O:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4](=[O:14])[CH3:13])=[CH:11][CH:10]=1)([O:27][CH3:28])=[O:26]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 566304374-Hydroxyphenylpropan-2-one ethylene ketal

Product 1

HCID 538253751-[4-(3-Carbomethoxyprop-2-eneoxy)phenyl]propan-2-oneYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-hydroxyphenylpropan-2-one ethylene ketal (3.0 g) and potassium carbonate (2.13 g) in acetone (50 ml) was treated with methyl 4-bromocrotonate (2.77 g) and a trace of potassium iodide. After heating under reflux for 12 hours, the solution was filtered, the solvent evaporated and the residue dissolved in methanol (50 ml) and 2.5 N hydrochloric acid (25 ml). The solution was stirred at ambient temperature for 2 hours, the solvent evaporated, the residue extracted with ether, washed with 2 N sodium hydroxide, water and dried (MgSO4). Removal of the solvent gave the title compound as an oil (2.3 g).

Workup

  1. temperatureAfter heating
  2. temperatureunder reflux for 12 hours
  3. filtrationthe solution was filtered
  4. customthe solvent evaporated
  5. dissolutionthe residue dissolved in methanol (50 ml)
  6. customthe solvent evaporated
  7. extractionthe residue extracted with ether
  8. washwashed with 2 N sodium hydroxide, water
  9. dry with materialdried (MgSO4)
  10. customRemoval of the solvent

Sources & evidence

ORD record
ord-3803c17dd5494cfa9f4c56420d7c5626
Source dataset
uspto-grants-1982_07
Patent number
US04338333

Linked notes

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