p-Toluenesulfonic acid → 2-(4-bromophenethoxy)tetrahydro-2H-pyran

HRID 1756014Notes

Reaction equation

HRID 1756014 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([CH2:17][CH2:18][OH:19])=[CH:15][CH:14]=1.[O:22]1[CH:27]=[CH:26][CH2:25][CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[O:19][CH2:18][CH2:17][C:16]1[CH:20]=[CH:21][C:13]([Br:12])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 728512-(4-Bromophenyl)ethanolHCID 516892Sodium Bicarbonate

Product 1

HCID 133067582-(4-bromophenethoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

p-Toluenesulfonic acid (0.30 g) was added to a solution of 4-bromophenethyl alcohol (9.50 g, 47.24 mmol) in methylene chloride (50 ml), and the mixture was stirred under ice-cooling. To the mixture was added 3,4-dihydropyran (5.53 g, 65.74 mmol). After stirring under ice-cooling for 20 minutes, a saturated aqueous solution of sodium bicarbonate (40 ml) was added to the reaction mixture. The resulting mixture was extracted with methylene chloride and dried over magnesium sulfate. After evaporation of the solvent, the desired 4-(2-(tetrahydropyran-2-yloxy)ethyl)bromobenzene was obtained (13.40 g, 99%).

Workup

  1. temperaturecooling
  2. stirringAfter stirring under ice-
  3. temperaturecooling for 20 minutes
  4. extractionThe resulting mixture was extracted with methylene chloride
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-a241b5a3077a404986abd9470ed4b4db
Source dataset
uspto-grants-1995_08
Patent number
US05439911

Reaction notes

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