4-Iodophenol → Methyl 11-(4-iodophenoxy)undecanoate

HRID 1989841Notes

Reaction equation

HRID 1989841 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].[I:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[I:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 223913Methyl 11-bromoundecanoate

Product 1

HCID 58773804Methyl 11-(4-iodophenoxy)undecanoateYield 81.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 11-bromoundecanoate (10 g, 35.8 mmmol), in acetone (150 ml) was treated with 4-iodophenol (7.88 g, 35.8 mmol) and potassium carbonate (9.88 g 71.6 mmol). The stirred reaction was heated at reflux for 48 h. The reaction was then allowed to cool and the reaction concentrated in vacuo to a gum. The reaction was then partitioned between ethyl acetate (150 ml) and water (150 ml). The ethyl acetate layer was separated dried, over sodium sulfate and concentrated in vacuo to solid. The solid was dissolved in diethyl ether (100 ml) and petroleum ether 60-80 C (100 ml) added. The solution was concentrated in vacuum to a volume of 100 ml. The solution was set aside and allowed to crystallise. The product was collected by filtration and dried in vacuum to give 12.22 g of solid. The mother liquors were concentrated to ˜20 ml and allowed to crystallise. A further 0.81 g of solid was collected by filtration. The two solids were combined to give the desired product (13.03 g, 86%) δH (CDCl3) 1.29-1.78 (16H, m, 3,4,5,6,7,8,9,10-CH2), 2.30 (2H, t, 2-CH2), 3.86 (3H, s, CO2CH3), 3.90 (2H, t, 11-CH2), 6.66 (2H, dd, 2,6-ArH), 7.53 (2H, dd, 3,5-ArH), δC(CDCl3) 24.90, 25.93, 29.09, 29.18, 29.30, 29.42, 34.07, 51.42, 68.06, 82.35, 116.90, 138.11, 158.98, and 174.33.

Workup

  1. customThe stirred reaction
  2. temperaturewas heated
  3. temperatureat reflux for 48 h
  4. temperatureto cool
  5. concentrationthe reaction concentrated in vacuo to a gum
  6. customThe reaction was then partitioned between ethyl acetate (150 ml) and water (150 ml)
  7. customThe ethyl acetate layer was separated
  8. dry with materialdried, over sodium sulfate
  9. concentrationconcentrated in vacuo to solid
  10. dissolutionThe solid was dissolved in diethyl ether (100 ml)
  11. additionpetroleum ether 60-80 C (100 ml) added
  12. concentrationThe solution was concentrated in vacuum to a volume of 100 ml
  13. customto crystallise
  14. filtrationThe product was collected by filtration
  15. customdried in vacuum

Sources & evidence

ORD record
ord-0da28bfd957d48ada0b0da846ebcb3d5
Source dataset
uspto-grants-2010_01
Patent number
US07642373B2

Reaction notes

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