Ethanol → Ethyl (4-iodophenyl)acetate

HRID 495077

Reaction equation

HRID 495077 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.OS(O)(=O)=O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:10][C:9](=[O:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([I:1])=[CH:7][CH:6]=1)[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 1372144-Iodophenylacetic acid

Product 1

HCID 14974990Ethyl (4-iodophenyl)acetateYield 90%

Procedure

4-Iodophenylacetic acid (3 g), ethanol (20 mL) and conc. H2SO4 (5 mL) were refluxed overnight. Ca. 15 mL ethanol was then evaporated, the residue was extracted with dichloromethane (3×100 mL), the combined organic extracts were washed with sat. aq. NaHCO3, dried over Na2SO4 and evaporated in vacuo to afford 2.97 g (90%) of 121JP58 as a yellow oil.

Workup

  1. custom15 mL ethanol was then evaporated
  2. extractionthe residue was extracted with dichloromethane (3×100 mL)
  3. washthe combined organic extracts were washed with sat. aq. NaHCO3
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb397d3af94241c2a8071375f0fb4a7e
Source dataset
uspto-grants-2009_05
Patent number
US07538222B2

Linked notes

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