3,4-dihydro-2H-pyran → 2H-Pyran, tetrahydro-2-(4-iodophenoxy)-

HRID 1768879Notes

Reaction equation

HRID 1768879 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1>CCCCCC>[O:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 108944-Iodophenol

Product 1

HCID 29168032H-Pyran, tetrahydro-2-(4-iodophenoxy)-Yield 77%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In 1 l of four-necked flask, 178 g (0.81 mol) of p-iodophenol, 81.68 g of dihydropyran and hexane were introduced and stirred for one hour. Then, 15 g of a cation exchange resin Amberlyst 15 (Rohm & Haas Co. "Amberlyst"®) was added thereto and stirred at room temperature overnight. Amberlyst 15 was removed by filtration and the filtrate was washed with an alkali and then with water. The oil layer was dried over sodium hydroxide and the solvent was distilled off to obtain 189.7 g (yield: 77%) of 4-[(tetrahydropyran-2-yl)oxy]iodobenzene.

Workup

  1. additionThen, 15 g of a cation exchange resin Amberlyst 15 (Rohm & Haas Co. "Amberlyst"®) was added
  2. stirringstirred at room temperature overnight
  3. customAmberlyst 15 was removed by filtration
  4. washthe filtrate was washed with an alkali and then with water
  5. dry with materialThe oil layer was dried over sodium hydroxide
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-b6f90781102743f783824218a542614e
Source dataset
uspto-grants-1995_01
Patent number
US05380461

Reaction notes

Loading…