4-Iodophenol → HCID 58773798, compound

HRID 1989839Notes

Reaction equation

HRID 1989839 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].[I:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[I:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoate

Product 1

HCID 58773798HCID 58773798, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 6-bromohexanoate (5.55 g, 25 mmol) in acetone (100 ml) was treated with 4-iodophenol (5.55 g, 25 mmol) and potassium carbonate (6.9 g 50 mmol). The stirred reaction was heated under reflux for 60 h. The reaction was then allowed to cool and the reaction concentrated in vacuum to a gum. The reaction was them partitioned between ethyl acetate (100 ml) and water (100 ml). The ethyl acetate layer was separated dried, over magnesium sulfate and concentrated in vacuo to give a colourless gum (8.71 g, 24.1 mmol, 96%), δH (CDCl3) 1.26 (3H, t, CO2CH2CH3), 1.46-1.81 (6H, m, 3,4,5-CH2), 2.33 (2H, t, 2-CH2), 3.91 (2H, t, 6-CH 2), 4.13 (2H, q, CO2CH2CH3), 6.66 (2H, dd, 2,6-ArH), 7.53 (2H, dd, 3,5-ArH), δH (CDCl3) 14.20, 24.60, 25.53, 28.75, 34.14, 60.20, 67.67, 82.44, 116.83,1 38.09, 158.84, and 173.52.

Workup

  1. customThe stirred reaction
  2. temperaturewas heated
  3. temperatureunder reflux for 60 h
  4. temperatureto cool
  5. concentrationthe reaction concentrated in vacuum to a gum
  6. custompartitioned between ethyl acetate (100 ml) and water (100 ml)
  7. customThe ethyl acetate layer was separated
  8. dry with materialdried, over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5bb9f982af6f424083486cd52587299c
Source dataset
uspto-grants-2010_01
Patent number
US07642373B2

Reaction notes

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