Ethanol → Ethyl 4-iodobenzoate

HRID 1076773Notes

Reaction equation

HRID 1076773 reaction equation
[CH:1]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=[C:3]([I:10])[CH:2]=1.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Na+].[Na+].[CH2:22](O)[CH3:23]>>[CH2:22]([O:8][C:7](=[O:9])[C:6]1[CH:5]=[CH:4][C:3]([I:10])=[CH:2][CH:1]=1)[CH3:23]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 120854-Iodobenzoic acid

Product 1

HCID 142891Ethyl 4-iodobenzoate

Procedure

A solution of 100 grams (0.403 mole) of p-iodobenzoic acid in 600 ml. of abs. ethanol containing 30 ml. of concentrated sulfuric acid is refluxed for 5 days. The cooled solution is poured over 350 grams of ice and is neutralized with saturated sodium carbonate solution. The oil that separates is extracted with six 150 ml. portions of ether. These ether extracts are combined, washed with water, dried over magnesium sulfate, and filtered. Evaporation of the ether gives 131.3 grams of ethyl-4-iodobenzoate as a chromatographically pure, clear, light oil.

Workup

  1. extractionThe oil that separates is extracted with six 150 ml
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customEvaporation of the ether

Sources & evidence

ORD record
ord-75d6721642b8463c9d81b2ec1964169e
Source dataset
uspto-grants-1976_05
Patent number
US03957871

Reaction notes

Loading…