Phenol → 2H-Pyran, tetrahydro-2-phenoxy-

HRID 129808Notes

Reaction equation

HRID 129808 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1>Cl.C(OCC)C>[O:7]([CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][O:8]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 80803,4-dihydro-2H-pyran

Product 1

HCID 1072402H-Pyran, tetrahydro-2-phenoxy-Yield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

Phenol (10 g, 106 mmol) was dissolved in 3,4-dihydro-2H-pyran (29 mL, 318 mmol) and one drop concentrated HCl was added at RT. The reaction was stirred at RT overnight. Ethyl ether (500 mL) was added to dilute the reaction. The organic layer was washed with water (2×100 mL), saturated sodium bicarbonate (2×100 mL), brine (2×100 mL) and dried over MgSO4. Evaporation gave title compound (17 g, 100%) as a colorless oil.

Workup

  1. additionto dilute
  2. customthe reaction
  3. washThe organic layer was washed with water (2×100 mL), saturated sodium bicarbonate (2×100 mL), brine (2×100 mL)
  4. dry with materialdried over MgSO4
  5. customEvaporation

Sources & evidence

ORD record
ord-403db72d7bdf442698f5afe331fccfc7
Source dataset
uspto-grants-1995_11
Patent number
US05470845

Reaction notes

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