Ethyl Acetate → 1-(3-Iodophenoxy)-3,6,9-trioxadecane

HRID 2226351Notes

Reaction equation

HRID 2226351 reaction equation
CS([O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15])(=O)=O.[I:16][C:17]1[CH:18]=[C:19](O)[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.CCCCCC>[I:16][C:17]1[CH:22]=[C:21]([CH:20]=[CH:19][CH:18]=1)[O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 122723-IodophenolHCID 126212722-(2-(2-Methoxyethoxy)ethoxy)ethyl methanesulfonate

Product 1

HCID 189870031-(3-Iodophenoxy)-3,6,9-trioxadecaneYield 61.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
68 °C

Procedure

To a solution of 1-[(methanesulfonyl)-oxy]-3,6,9-trioxadecane (11.6 g, 47.9 mmol) in dry DMF (145 ml) was added 3-iodophenol (10.6 g, 48.2 mmol) and potassium carbonate (6.6 g, 47.8 mmol). The reaction was immersed in an oil bath which was warmed to 68° C. over a period of 0.5 hr. The reaction was stirred at this temperature under an N2 atmosphere for 16 hrs and then at 82° C. for an additional 2 hrs. At the end of this period, the reaction was cooled, diluted with DMF, filtered through a pad of celite and evaporated in vacuo. The resulting residue was taken up into ethyl acetate (500 ml), washed with water (200 ml), 1 N aqueous sodium hydroxide (200 ml) and brine (200 ml), dried (Na2SO4), filtered and evaporated in vacuo to provide a light brown oil. Flash column chromatography (silica, 1:3 to 1:2; EtOAc:hexane) provided 1-(3-iodophenoxy)-3,6,9-trioxadecane as a light yellow oil (10.8 g, 37.1%). Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired product. Calculated for C13H10O4I:C,42.52; H, 5.49; I, 34.56. Found: C, 42.50, H, 5.13; I, 34.78.

Workup

  1. customThe reaction was immersed in an oil bath
  2. waitat 82° C. for an additional 2 hrs
  3. temperatureAt the end of this period, the reaction was cooled
  4. filtrationfiltered through a pad of celite
  5. customevaporated in vacuo
  6. washwashed with water (200 ml), 1 N aqueous sodium hydroxide (200 ml) and brine (200 ml)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto provide a light brown oil

Sources & evidence

ORD record
ord-50118abdaa674894938c7b70a831659c
Source dataset
uspto-grants-1994_09
Patent number
US05348727

Reaction notes

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