Water → HCID 58773792, compound

HRID 1989840Notes

Reaction equation

HRID 1989840 reaction equation
[I:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[CH:4][CH:3]=1.O.[OH-].[Na+]>C(O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 58773798HCID 58773798, compound

Product 1

HCID 58773792HCID 58773792, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 6-(4-iodophenoxy)hexanoate (3.62 g, 10 mmol), in ethanol (30 ml), water (30 ml) was treated with sodium hydroxide (1 g, 25 mmol) and the reaction was stirred under reflux for 3 h. The reaction was then allowed to cool and concentrated in vacuum to a solid. The solid was then treated cautiously with ethyl acetate (100 ml) and 1N hydrochloric acid (100 ml) and the reaction stirred at room temperature for 10 min. The ethyl acetate layer was separated dried over sodium sulfate and concentrated in vacuum to give a pale yellow solid (3.11 g, 9.3 mmol, 93%), δH (CDCl3) 1.48-1.82 (6H, m, 3,4,5-CH2), 2.40 (2H, t, 2-CH2), 3.91 (2H, t, 6-CH2O), 6.67 (2H, dd, 2,6-ArH), 7.53 (2H, dd, 3,5-ArH), δc (CDCl3) 24.31, 25.50, 38.75, 33.89, 82.54, 116.87, 138.14, 158.83 and 179.97

Workup

  1. temperatureunder reflux for 3 h
  2. temperatureto cool
  3. concentrationconcentrated in vacuum to a solid
  4. additionThe solid was then treated cautiously with ethyl acetate (100 ml) and 1N hydrochloric acid (100 ml)
  5. stirringthe reaction stirred at room temperature for 10 min
  6. customThe ethyl acetate layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-4929c9af9a3446f3bb90ded685aa312a
Source dataset
uspto-grants-2010_01
Patent number
US07642373B2

Reaction notes

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