Water → 4-bromo-2-propyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenol

HRID 552446Notes

Reaction equation

HRID 552446 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][CH3:11])[C:3]=1[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:26]1[CH:31]=[CH:30][CH2:29][CH2:28][CH2:27]1.O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH2:10][CH3:11])[C:3]=1[CH2:12][O:13][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][O:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 579008284-Bromo-3-(hydroxymethyl)-2-propylphenol

Product 1

HCID 579007894-bromo-2-propyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]phenolYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-3-(hydroxymethyl)-2-propylphenol (1.04 g, 4.24 mmol) in dichloromethane (50 mL), p-toluenesulfonic acid-hydrate (81 mg, 0.424 mmol) and 3,4-dihydro-2H-pyrane (535 mg, 6.36 mmol) were added at room temperature. The mixture was stirred at same temperature for 5 hours. The reaction solution was added with water and extracted with chloroform. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated in vacuum. The residue was purified by silica-gel column chromatography (hexane/ethyl acetate) and the title compound (972 mg, 70%) was obtained as colorless oil.

Workup

  1. extractionextracted with chloroform
  2. washSubsequently, the organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d0b79bdfb69d4727acf3ad2ad6ab353e
Source dataset
uspto-grants-2011_05
Patent number
US07951822B2

Reaction notes

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