4-Iodophenol → 2H-Pyran, tetrahydro-2-(4-iodophenoxy)-

HRID 1158603Notes

Reaction equation

HRID 1158603 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.O[CH:10]1[C:15](O)=[CH:14][CH:13]=[CH:12][O:11]1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH:10]1[O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 108944-IodophenolHCID 516892Sodium BicarbonateHCID 19065318HCID 19065318, compound

Product 1

HCID 29168032H-Pyran, tetrahydro-2-(4-iodophenoxy)-Yield 98%

Reagents, catalysts & solvents 2

HCID 22033616Pyridinium.p-toluenesulfonateCatalystHCID 1140TolueneSolvent

Procedure

20 g (89 mmol) of 4-iodophenol was dissolved in 45 ml (2.0 mol/l) of toluene. To this was added 16.4 ml (0.18 mol) of 2,3-dihydroxypyrane and 1.15 g (4.5 mmol) of pyridinium p-toluenesulfonic acid, and the mixture was stirred for 2 hours under a nitrogen atmosphere. After completion of the reaction, a saturated sodium hydrogen carbonate aqueous solution was added and the mixture was extracted with ethyl acetate, then, the organic layer was washed with water, and the solvent was distilled off. As a result, 26.5 g (87.1 mmol) of (h) was obtained. The yield was 98% based on 4-iodophenol.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-634333fed36947c0ad058bb99d31626b
Source dataset
uspto-grants-2010_10
Patent number
US07811467B2

Reaction notes

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