HCID 13011787, compound → 6-Ethoxy-2-methyl-2H-pyran-3(6H)-one

HRID 1439378Notes

Reaction equation

HRID 1439378 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[CH:6]=[CH:5][CH:4]([OH:9])[O:3]1.C([O-])([O-])O[CH2:12][CH3:13]>C1C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[CH3:1][CH:2]1[C:7](=[O:8])[CH:6]=[CH:5][CH:4]([O:9][CH2:12][CH3:13])[O:3]1

Participants

5

Reactant 2

HCID 13011787HCID 13011787, compoundHCID 53630039Ethylorthoformate

Product 1

HCID 145471086-Ethoxy-2-methyl-2H-pyran-3(6H)-oneYield 85%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 241BenzeneSolvent

Procedure

A 12.8 g quantity of 2-methyl-6-hydroxy-3-oxo-3,6-dihydro-2H-pyran and 14.8 g of ethyl orthoformate are reacted in the presence of 1 g of zinc chloride in 100 ml of benzene with refluxing for 120 minutes. After the reaction, the benzene is distilled off, the residue is poured into 50 ml of water and the mixture is extracted three times with 50 ml portions of ether. The ethereal layer is washed with an aqueous solution of sodium carbonate and then dried over magnesium sulfate. After removing the magnesium sulfate, the dried mass is distilled to remove the ether, and the residue is distilled at a reduced pressure of 30 mm Hg to give 12 g of 2-methyl-6-ethoxy-3-oxo-3,6-dihydro-2H-pyran as a yellow liquid fraction at 82° to 85° C in a yield of 85%.

Workup

  1. temperaturewith refluxing for 120 minutes
  2. customAfter the reaction
  3. distillationthe benzene is distilled off
  4. additionthe residue is poured into 50 ml of water
  5. extractionthe mixture is extracted three times with 50 ml portions of ether
  6. washThe ethereal layer is washed with an aqueous solution of sodium carbonate
  7. dry with materialdried over magnesium sulfate
  8. customAfter removing the magnesium sulfate
  9. distillationthe dried mass is distilled
  10. customto remove the ether
  11. distillationthe residue is distilled at a reduced pressure of 30 mm Hg

Sources & evidence

ORD record
ord-c52ec922832d439da663bd0eb7aa25eb
Source dataset
uspto-grants-1977_11
Patent number
US04059595

Reaction notes

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