Acetone → HCID 12355869, compound

HRID 435844Notes

Reaction equation

HRID 435844 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=2[CH:3]=1.[C:18](=[O:21])([O-])[O-].[K+].[K+].[I-].[K+].[CH3:26][C:27]([CH3:29])=[O:28]>>[C:27]([C:29]1[CH:6]=[CH:7][C:8]([O:9][CH2:4][CH2:3][CH2:2][CH2:17][CH2:16][O:1][C:2]2[CH:17]=[CH:16][C:5]3[C:6](=[O:15])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=3[CH:3]=2)=[CH:10][C:18]=1[OH:21])(=[O:28])[CH3:26]

Participants

5

Reactant 4

HCID 180AcetoneHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 5376802ethyl 7-hydroxy-4-oxo-4H-chromen-2-carboxylate

Product 1

HCID 12355869HCID 12355869, compound

Procedure

A mixture of 3.05 parts of 4-(5-bromopentyloxy)-2-hydroxy acetophenone, 2.34 parts of ethyl 7-hydroxy-4-oxo-4H-1-benzopyran-2-carboxylate, 1.38 parts of potassium carbonate and 0.5 parts of potassium iodide, in 200 parts of dry acetone, was heated under reflux for 24 hours. The solution was filtered while hot and the inorganic salts washed with hot acetone. The solvent was removed to leave a yellow solid, which was washed with water and ether. The insoluble yellow solid was crystallised from ethyl alcohol to yield 3.3 parts of ethyl 7-[5-(4-acetyl-3-hydroxyphenoxy)pentyloxy]-4-oxo-4H-1-benzopyran-2-carboxylate as pale yellow needles, melting point 136°-137° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. filtrationThe solution was filtered while hot and the inorganic salts
  3. washwashed with hot acetone
  4. customThe solvent was removed
  5. customto leave a yellow solid, which
  6. washwas washed with water and ether
  7. customThe insoluble yellow solid was crystallised from ethyl alcohol

Sources & evidence

ORD record
ord-4b7444afa23f4ff8a37cb22991b90a32
Source dataset
uspto-grants-1977_02
Patent number
US04006245

Reaction notes

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