Dodecanoyl chloride → HCID 15222637, compound

HRID 1492108Notes

Reaction equation

HRID 1492108 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[I:15][C:16]1[CH:21]=[C:20]([I:22])[CH:19]=[C:18]([I:23])[C:17]=1[OH:24]>C(#N)C>[C:1]([O:24][C:17]1[C:16]([I:15])=[CH:21][C:20]([I:22])=[CH:19][C:18]=1[I:23])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 8166Dodecanoyl chlorideHCID 118622,4,6-Triiodophenol

Product 1

HCID 15222637HCID 15222637, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dodecanoyl chloride (2.95 ml, 12.8 mmol) was added to a suspension of 2,4,6-triiodophenol (6.0 g, 12.7 mmol) in refluxing acetonitrile (50 ml) and the mixture was heated under argon for 24 hrs. The reaction mixture was cooled and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness under vacuum to give an off-white solid. The crude product was recrystallized from methanol to give 6.9 g (83%) of the desired ester, mp 68°-69° C.

Workup

  1. temperaturethe mixture was heated under argon for 24 hrs
  2. temperatureThe reaction mixture was cooled
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness under vacuum
  7. customto give an off-white solid
  8. customThe crude product was recrystallized from methanol

Sources & evidence

ORD record
ord-50ee9dad52a9487fbd16acad77eda513
Source dataset
uspto-grants-1994_12
Patent number
US05372800

Reaction notes

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