2-chloro-1-(4-hydroxy-3-methoxyphenyl)ethanone → HCID 15020343, compound

HRID 1460228Notes

Reaction equation

HRID 1460228 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH3:13])[CH:6]=1)=[O:4].[C:14]([O-:17])(=[O:16])[CH3:15].[K+]>C(O)C.C(O)(=O)C>[C:14]([O:17][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH3:13])[CH:6]=1)=[O:4])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 2421842-chloro-1-(4-hydroxy-3-methoxyphenyl)ethanoneHCID 517044Potassium Acetate

Product 1

HCID 15020343HCID 15020343, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a slurry of 80.2 g (0.4 mole) of 2-chloro-1-(4-hydroxy-3-methoxyphenyl)ethanone in 576 ml of absolute ethanol and 24 ml of glacial acetic acid was added 73.6 g (0.75 mole) of potassium acetate, and the mixture was heated at reflux temperature for 1 hr. The mixture was cooled, filtered, and the filtrate concentrated to a gummy residue. The residue was triturated with four 200 ml portions of hot benzene. The combined extracts were washed with three 200 ml portions of saturated aqueous sodium bicarbonate solution and once with brine, dried over sodium sulfate, and concentrated to give a solid residue. The solid was recrystallized from benzene (with charcoal treatment) to yield 32.4 g (36% yield) of the title compound as a white solid, mp 115°-117° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 1 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated to a gummy residue
  6. customThe residue was triturated with four 200 ml portions of hot benzene
  7. washThe combined extracts were washed with three 200 ml portions of saturated aqueous sodium bicarbonate solution and once with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto give a solid residue
  11. customThe solid was recrystallized from benzene (with charcoal treatment)

Sources & evidence

ORD record
ord-7e7bc592e91741d99f9b5b5daa1b8b27
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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