3-Iodo-4-methylbenzoic acid → Ethyl 3-iodo-4-methylbenzoate

HRID 1255955Notes

Reaction equation

HRID 1255955 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[C:12](OCC)(=O)[CH3:13].CCCCCC>C(O)C.S(=O)(=O)(O)O>[I:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([O:7][CH2:12][CH3:13])=[O:6]

Participants

5

Reactant 2

HCID 6216403-Iodo-4-methylbenzoic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 23073518Ethyl 3-iodo-4-methylbenzoateYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 3-iodo-4-methylbenzoic acid (1.5 g, 5.7 mmol) in 25 ml of ethanol was dropped in 0.5 ml of concentrated sulfuric acid. The reaction was refluxed overnight. TLC (Ethyl Acetate/Hexane 1:10) indicated the completion of the esterification. The extra ethanol was evaporated and the residue was dissolved in 30 ml of dichloromethane, which was washed with water (10 ml) and brine (10 ml), dried, and evaporated to a thick oil. A white solid was obtained after drying under vacuo (1.56 g. in 95% yield).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. customThe extra ethanol was evaporated
  3. dissolutionthe residue was dissolved in 30 ml of dichloromethane
  4. washwhich was washed with water (10 ml) and brine (10 ml)
  5. customdried
  6. customevaporated to a thick oil
  7. customA white solid was obtained
  8. customafter drying under vacuo (1.56 g. in 95% yield)

Sources & evidence

ORD record
ord-efd5ea6e23c7490e82e1285f66ba3d3a
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

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