Benzyl Chloride → Methyl 3-benzyl-4-iodobenzoate

HRID 1361090Notes

Reaction equation

HRID 1361090 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[I:20])[C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:1]([C:10]1[CH:11]=[C:12]([CH:17]=[CH:18][C:19]=1[I:20])[C:13]([O:15][CH3:16])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 66971745Methyl 3-benzyl-4-iodobenzoateYield 105.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

47 ml (411 mmol) of benzyl chloride are added to a solution of 104 g (374 mmol) of methyl 3-hydroxy-4-iodobenzoate and 103 g (748 mmol) of potassium carbonate in 600 ml of methyl ethyl ketone, and the reaction medium is then refluxed for 8 hours. After cooling, the reaction medium is filtered, the precipitate is rinsed with ethyl acetate and the filtrate is evaporated to dryness. The residue is taken up in a mixture of water and ethyl acetate. The organic phase is dried over sodium sulfate, filtered and evaporated. 139 g (100%) of methyl 3-benzyl-4-iodobenzoate are obtained in the form of a white solid.

Workup

  1. temperaturethe reaction medium is then refluxed for 8 hours
  2. temperatureAfter cooling
  3. filtrationthe reaction medium is filtered
  4. washthe precipitate is rinsed with ethyl acetate
  5. customthe filtrate is evaporated to dryness
  6. additionThe residue is taken up in a mixture of water and ethyl acetate
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-bc02926280b744a2ac545cce46f0c0d0
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

Loading…