Potassium Carbonate → HCID 67698975, compound

HRID 1034392Notes

Reaction equation

HRID 1034392 reaction equation
I[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([I:9])[C:3]=1O.[C:11](=[O:14])([O-])[O-].[K+].[K+]>CN(C)C=O>[I:8][CH:6]1[CH2:5][CH:4]([I:9])[CH2:3][CH:7]1[CH2:2][O:14][C:11]1[C:6]([I:8])=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 118622,4,6-Triiodophenol

Product 1

HCID 67698975HCID 67698975, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 36.2 g (0.08 mol) of 2,4,6-triiodophenol, 12.5 g (0.08 mol) of bromomethyleyelopentane [Noller and Adams, J. Org. Chem., 48, 1080-9 (1926)] and 10.6 g (0.08 mol) of milled anhydrous potassium carbonate in 100 ml dry dimethylformamide was heated at 100° C. under argon for 3.5 hrs. The mixture was cooled and concentrated in vacuo. The resulting residue was combined with 100 ml of ice-cold water and the oily product was extracted with ethyl acetate (3×100 ml). The combined ethyl acetate extracts were dried (MgSO4) and concentrated in vacuo to a dark oil. The oil was purified by chromatography (neutral alumina eluted by hexanes) to yield 24.0 g (57%) of the desired product as an oil. Bp: 220°-5° C./1 atm.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. extractionthe oily product was extracted with ethyl acetate (3×100 ml)
  4. dry with materialThe combined ethyl acetate extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo to a dark oil
  6. customThe oil was purified by chromatography (neutral alumina eluted by hexanes)

Sources & evidence

ORD record
ord-aba834f4faa94731ae29301085a1685f
Source dataset
uspto-grants-1994_05
Patent number
US05316755

Reaction notes

Loading…