Methyl iodide → HCID 20134169, compound

HRID 1906954Notes

Reaction equation

HRID 1906954 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][C:13](=[O:15])[CH3:14])[CH:8]=[CH:9][C:10]=1[OH:11])([O:3][CH3:4])=[O:2].IC.[C:18](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH2:12][C:13](=[O:15])[CH3:14])[CH:8]=[CH:9][C:10]=1[O:11][CH3:18])([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 18627998Methyl 2-hydroxy-5-(2-oxopropyl)benzoate

Product 1

HCID 20134169HCID 20134169, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(3-carbomethoxy-4-hydroxyphenyl)propan-2-one (3.0 g), iodomethane (5.0 g), potassium carbonate (7.0 g) was refluxed in acetone until tlc showed no starting material (~6 hours). The mixture was cooled, filtered and evaporated. The residue was partitioned between ether and water and the layers separated. The ether layer was dried (MgSO4) and evaporated to give the title compound (3.2 g). τ(CDCl3) 7.84 (3H, s), 6.35 (2H, s), 6.1 (3H, s), 3.05 (1H, d, J=8 Hz), 2.68 (1H, dd, J=8 Hz, J=2 Hz), 2.36 (1H, d, J=2 Hz).

Workup

  1. customno starting material (~6 hours)
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was partitioned between ether and water
  6. customthe layers separated
  7. dry with materialThe ether layer was dried (MgSO4)
  8. customevaporated

Sources & evidence

ORD record
ord-773662b23ed44b8bad058f2639ff567a
Source dataset
uspto-grants-1987_03
Patent number
US04654371

Reaction notes

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