4-Benzoyloxy-1-hydroxy-1-hexene-3,5-dione → 3-(Benzoyloxy)-2-methyl-4H-pyran-4-one

HRID 1461541Notes

Reaction equation

HRID 1461541 reaction equation
[C:1]([O:9][CH:10]([C:16](=[O:18])[CH3:17])[C:11](=[O:15])[CH:12]=[CH:13]O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[C:1]([O:9][C:10]1[C:11](=[O:15])[CH:12]=[CH:13][O:18][C:16]=1[CH3:17])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 679144844-Benzoyloxy-1-hydroxy-1-hexene-3,5-dione

Product 1

HCID 802553-(Benzoyloxy)-2-methyl-4H-pyran-4-oneYield 81.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Benzoyloxy-1-hydroxy-1-hexene-3,5-dione (54.20 g, 218 mmol) is refluxed for 2 hours in 400 ml of acetic acid, the reaction mixture is concentrated at 40° C. on a rotary evaporator, the residue is dissolved in 500 ml of dichloromethane and washed twice with 300 ml of saturated sodium bicarbonate solution. The organic phase is dried over magnesium sulphate, concentrated on a rotary evaporator and gives 40.75 g (81.2%) of 3-benzoyloxy-2-methyl-4-pyrone, content 73%, m.p.: 106°-110° C.

Workup

  1. concentrationthe reaction mixture is concentrated at 40° C. on a rotary evaporator
  2. dissolutionthe residue is dissolved in 500 ml of dichloromethane
  3. washwashed twice with 300 ml of saturated sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-c4ade3ba5ef4402c9430bb0ff261f7d1
Source dataset
uspto-grants-1991_12
Patent number
US05075461

Reaction notes

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