Benzyl Chloride → 3-Benzyloxy-2-ethyl-4-pyrone

HRID 374446

Reaction equation

HRID 374446 reaction equation
[CH2:1]([C:3]1[O:4][CH:5]=[CH:6][C:7](=[O:10])[C:8]=1[OH:9])[CH3:2].[OH-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CO>[CH2:13]([O:9][C:8]1[C:7](=[O:10])[CH:6]=[CH:5][O:4][C:3]=1[CH2:1][CH3:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 21059Ethyl Maltol

Product 1

HCID 105855423-Benzyloxy-2-ethyl-4-pyroneYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-ethyl-3-hydroxy-4-pyrone (70 g, 0.5 mol) in methanol (650 ml) and sodium hydroxide solution (24 g, 0.6 mol of sodium hydroxide dissolved in 80 ml distilled water) was added benzyl chloride (90 ml, 0.75 mol) with stirring at room temperature. The reaction mixture was refluxed for 24 hours and then cooled. The solvent was removed by rotary evaporation and the residue was extracted into dichloromethane (500 ml). The organic layer was washed with 5% w/v sodium hydroxide solution (3×600 ml) and water (2×600 ml), dried over anhydrous sodium sulphate, filtered and rotary evaporated to give an oil. This oil was crystallized from diethylether in liquid nitrogen and the product recrystallized from diethylether to give the title compound (69 g, 65%) as colourless crystals, m.p. 33°-34° C.

Workup

  1. temperatureThe reaction mixture was refluxed for 24 hours
  2. temperaturecooled
  3. customThe solvent was removed by rotary evaporation
  4. extractionthe residue was extracted into dichloromethane (500 ml)
  5. washThe organic layer was washed with 5% w/v sodium hydroxide solution (3×600 ml) and water (2×600 ml)
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customrotary evaporated
  9. customto give an oil
  10. customThis oil was crystallized from diethylether in liquid nitrogen
  11. customthe product recrystallized from diethylether

Sources & evidence

ORD record
ord-9f0d33d0a2f14335a2d242948edd4cec
Source dataset
uspto-grants-1996_01
Patent number
US05480894

Linked notes

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