Iodoethane → Methyl 3-formylbenzoate

HRID 1531805Notes

Reaction equation

HRID 1531805 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH:7]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1C(O)=O)=[O:8].[CH2:18](I)C>C(#N)C>[CH:7]([C:9]1[CH:10]=[C:14]([CH:15]=[CH:16][CH:17]=1)[C:1]([O:2][CH3:18])=[O:4])=[O:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8406Phthalaldehydic acidHCID 11430Potassium Carbonate

Product 1

HCID 639145Methyl 3-formylbenzoateYield 89.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potasium carbonate (6.84 g) was added to a solution of 3 formylbenzoic acid (5.00 g), ethyl iodide (5.15 g) in acetonitrile (100 ml). The reaction mixture was refluxed for 18 hrs after cooling the mixture was partitioned between ethyl acetate and water, the organic phase separated, washed with saturated brine, dried over MgSO4 and evaporated under reduced pressure to afford the title compound as a yellow oil (4.84 g).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hrs
  2. temperatureafter cooling the mixture
  3. customwas partitioned between ethyl acetate and water
  4. customthe organic phase separated
  5. washwashed with saturated brine
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e8f477bfa98d4059b099bbf7298f97e5
Source dataset
uspto-grants-2001_03
Patent number
US06200978B1

Reaction notes

Loading…