p-Toluenesulfonic acid → 2H-Pyran, tetrahydro-2-(4-iodophenoxy)-

HRID 2291352Notes

Reaction equation

HRID 2291352 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.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C>[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

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 108944-Iodophenol

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10 Grams of p-iodophenol, 8 ml of dihydropyrane and a catalytic amount of p-toluenesulfonic acid was dissolved in 30 ml of anhydrous diethyl ether, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with water, dried then the solvent was removed by evaporation to yield 12.4 g of 4-(2-tetrahydropyranyloxy)-1-iodobenzene in the form of yellow oily substance. Boiling point: 84°-87° C. (at 25 mm Hg).

Workup

  1. washThe reaction mixture was washed with water
  2. customdried
  3. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-a14ba10efab34592a258f36ac5975bb4
Source dataset
uspto-grants-1989_01
Patent number
US04795814

Reaction notes

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