p-Toluenesulfonic acid → 2-(2-Bromoethoxy)tetrahydro-2H-pyran

HRID 399635Notes

Reaction equation

HRID 399635 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:18][CH2:19][CH2:20][OH:21]>C(Cl)Cl>[Br:18][CH2:19][CH2:20][O:21][CH:6]1[CH2:5][CH2:4][CH2:3][CH2:2][O:1]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 108982-Bromoethanol

Product 1

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

12 ml of dihydropyran and 20 mg of paratoluenesulphonic acid are added to a solution of 3.7 ml of 2-bromoethanol dissolved in 100 ml of methylene chloride. After stirring for 3 hours at 20° C., the reaction medium is washed with water and then with saturated aqueous sodium chloride, and evaporated to dryness. The residue is distilled at 90° C. at a pressure of 0.5 mbar.

Workup

  1. washthe reaction medium is washed with water
  2. customwith saturated aqueous sodium chloride, and evaporated to dryness
  3. distillationThe residue is distilled at 90° C. at a pressure of 0.5 mbar

Sources & evidence

ORD record
ord-5636258cc0ce474cbf963f08111651a1
Source dataset
uspto-grants-1998_10
Patent number
US05821255

Reaction notes

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