Acetyl chloride → Ethyl 5-iodo-2-methoxybenzoate

HRID 1598982Notes

Reaction equation

HRID 1598982 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13](Cl)(=O)[CH3:14]>C(O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH2:13][CH3:14])=[O:8]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 40861665-Iodo-2-methoxybenzoic acid

Product 1

HCID 18931281Ethyl 5-iodo-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-iodo-2-methoxybenzoic acid (13.4 g, 48 mmol), acetyl chloride (1 mL) and ethanol (50 mL) was heated 4 hours with stirring at reflux. The mixture was concentrated and the residue was dissolved in diethyl ether. The solution was poured into ice-cold saturated sodium bicarbonate and the organic phase was washed with brine, dried (K2 CO3), filtered and concentrated to give ethyl 5-iodo-2-methoxybenzoate (13.5 g, 44 mmol) as an oil.

Workup

  1. temperaturewas heated 4 hours
  2. temperatureat reflux
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in diethyl ether
  5. additionThe solution was poured into ice-cold saturated sodium bicarbonate
  6. washthe organic phase was washed with brine
  7. customdried (K2 CO3)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9a6cf375510a4d7fa9cb0e51fc06d70a
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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