3,4-dihydro-2H-pyran → 4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanol

HRID 1269805Notes

Reaction equation

HRID 1269805 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH:7]1([OH:14])[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9][CH2:8]1>C1(C)C=CC=CC=1>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:13][CH:10]1[CH2:11][CH2:12][CH:7]([OH:14])[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 111621,4-Cyclohexanediol

Product 1

HCID 118201114-(tetrahydro-2H-pyran-2-yloxy)cyclohexanolYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

An acidic resin (Dowex 50W×8, trade name, Dow Chemical Company, 800 mg) and dihydropyran (1.89 ml, 20.7 mol) were added dropwise to a solution of 1,4-cyclohexanediol (4.0 g, 34.4 mol) in toluene (80 ml) at room temperature and vigorously stirred. After 17 hours, the reaction mixture was filtered by the use of Celite and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 4-(tetrahydro-2H-pyran-2-yloxy)cyclo-hexanol (2.69 g, 65%).

Workup

  1. filtrationthe reaction mixture was filtered by the use of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0a51389b750f4a9c80388af32c79e852
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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