Acetyl chloride → 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one

HRID 555628Notes

Reaction equation

HRID 555628 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[CH:3]=1.[C:10](Cl)(=[O:12])[CH3:11]>FC(F)(F)C(O)=O>[C:10]([C:3]1[C:4](=[O:9])[O:5][C:6]([CH3:8])=[CH:7][C:2]=1[OH:1])(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 546784943-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-oneYield 34.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Dissolve 4-hydroxy-6-methyl-pyran-2-one (12.6 g, 100 mmol) in trifluoroacetic acid (50 ml). and add 7.8 g (100 mml) of acetyl chloride dropwise. Heat this mixture at reflux for 5 hours. Evaporate the reaction mixture under reduced pressure. Add 50 ml of water, extract with ethyl acetate (50 ml×3) and combine the organic layers. Wash with brine and dry (sodium sulfate). Chromatograph on silica gel, eluting with chloroform to provide 5.8 g (34.5 mmol) of 3-acetyl-4-hydroxy-6-methyl-pyran-2-one.

Workup

  1. temperatureHeat this mixture
  2. temperatureat reflux for 5 hours
  3. customEvaporate the reaction mixture under reduced pressure
  4. additionAdd 50 ml of water
  5. extractionextract with ethyl acetate (50 ml×3)
  6. washWash with brine
  7. dry with materialdry (sodium sulfate)
  8. washChromatograph on silica gel, eluting with chloroform

Sources & evidence

ORD record
ord-acc49a96cc2d42188669d9181dbb37b2
Source dataset
uspto-grants-2011_11
Patent number
US08053458B2

Reaction notes

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