Hydrochloric Acid → Ethyl 4-iodobenzoate

HRID 2420655Notes

Reaction equation

HRID 2420655 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl.[CH2:12](O)[CH3:13]>>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:12][CH3:13])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 120854-Iodobenzoic acid

Product 1

HCID 142891Ethyl 4-iodobenzoate

Procedure

A mixture of 4-iodobenzoic acid, 25 ml ethyl alcohol and 20 ml solution of dry HCl in ethyl alcohol was refluxed for 2 hours. The solid was dissolved after 1 hour of boiling. The reaction solution was cooled to room temperature and evaporated under vacuum to a volume of 10 ml. A lower organic layer formed with the chemical conversion of the acid to the ester. The resulting mixture was cooled in an ice bath. To this mixture 80 ml of diethyl ether, dry sodium hydrogen carbonate (1 gram) and 50 grams of ice were added. This solution was stirred, washed by dissolution of a saturated solution of sodium bicarbonate in 50 ml water and water, dried over sodium sulfate, and evaporated under vacuum, yielding ethyl 4-iodobenzoate as a liquid oil product (5.43 gram, 96.1% yield) [1H-NMR (CDCl3): d7.8 (s, 1H), d7.79 (s, 1H), 7.6 (s, 1H), d4.4 (d, 2H, J=7.1 Hz), d1.4 (s, 3H)].

Workup

  1. temperaturewas refluxed for 2 hours
  2. dissolutionThe solid was dissolved after 1 hour of boiling
  3. customevaporated under vacuum to a volume of 10 ml

Sources & evidence

ORD record
ord-2eae7bd8d4d44b7b93e48a63af18fd22
Source dataset
uspto-grants-2011_06
Patent number
US07955852B2

Reaction notes

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