Potassium Iodide → Methyl 4-(2-oxopropoxy)benzoate

HRID 580630Notes

Reaction equation

HRID 580630 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:13][C:14](=[O:16])[CH3:15].[I-].[K+]>CC(C)=O>[C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:13][C:14](=[O:16])[CH3:15])=[CH:11][CH:10]=1)([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 7456Methylparaben

Product 1

HCID 21832186Methyl 4-(2-oxopropoxy)benzoateYield 188.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methyl 4-hydroxybenzoate (30.4 g), chloroacetone (8.5 g) potassium carbonate (54 g) and potassium iodide (33.3 g) was refluxed in acetone for 4 hours. The reaction mixture was cooled, the solids filtered and the solvent evaporated. The residue was partitioned between water and ether, the layers separated and the organic layer dried (MgSO4). Removal of the solvent gave the title compound (36 g). τ (CDCl3) 7.75 (3H, s), 6.11 (3H, s), 5.39 (2H, s), 3.09 (2H, d, J=9 Hz), 2.0 (2H, d, J=9 Hz).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe solids filtered
  3. customthe solvent evaporated
  4. customThe residue was partitioned between water and ether
  5. customthe layers separated
  6. dry with materialthe organic layer dried (MgSO4)
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-171d7eab1190475c99124135f6f4076d
Source dataset
uspto-grants-1988_06
Patent number
US04753962

Reaction notes

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