Acetic Acid → 2-Acetyl-3-hydroxy-6-phenyl-4H-pyran-4-one

HRID 1747774Notes

Reaction equation

HRID 1747774 reaction equation
[C:1]1([C:7](=[O:17])[CH2:8][C:9](=[O:16])[C:10](=[O:15])[CH2:11][C:12](=[O:14])[CH3:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.C(O)(=O)C>O>[C:12]([C:11]1[O:17][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][C:9](=[O:16])[C:10]=1[OH:15])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12217721Iodo benzene diacetateHCID 132009181-Phenylheptane-1,3,4,6-tetrone

Product 1

HCID 132009232-Acetyl-3-hydroxy-6-phenyl-4H-pyran-4-oneYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-phenylheptane-1,3,4,6-tetrone (2.3 g), iodobenzene diacetate (6.7 g) and acetic acid (80 mL) was stirred at room temperature for 16 hr, the reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.32 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-00344df25fe243fab4fc1cd6298b2e0f
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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