Methyl iodide → Methyl 2-formylbenzoate

HRID 1939399Notes

Reaction equation

HRID 1939399 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([OH:3])=[O:2].IC.[C:14](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O:3][CH3:14])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8406Phthalaldehydic acidHCID 11430Potassium Carbonate

Product 1

HCID 243003Methyl 2-formylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.5 g (30 mmol) of 2-carboxybenzaldehyde, 17.1 g (120 mmol) of iodomethane and 12.4 g (90 mmol) of potassium carbonate were stirred in 85 ml of acetone for 24 hours. The solvent was removed by evaporation and the residue was partioned between 50 ml of water and 50 ml of ether. The aqueous layer was washed with 3×50 ml portions of ether. The combined organic extracts were washed with 30 ml each of 1M sodium thiosufate and saturated sodium cloride solutions and dried over MgSO4. The solvent was removed by evaporation. The residue was subjected to flash chromatography (silica gel, 10% ethyl acetate/hexanes) to give the title compound as a clear colorles oil.

Workup

  1. customThe solvent was removed by evaporation
  2. washThe aqueous layer was washed with 3×50 ml portions of ether
  3. washThe combined organic extracts were washed with 30 ml each of 1M sodium thiosufate and saturated sodium cloride solutions
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-b5b7d400581143bfbaeb84497dabafa5
Source dataset
uspto-grants-1997_12
Patent number
US05696162

Reaction notes

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