HCID 19744879, compound → 1-Propanone, 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-

HRID 2254269Notes

Reaction equation

HRID 2254269 reaction equation
COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[C:15](=[O:32])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24]COC)=[C:20]([O:28]COC)[CH:19]=1>Cl.CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[C:15](=[O:32])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([OH:28])[CH:19]=1

Participants

3

Reactant 1

HCID 19744879HCID 19744879, compound

Product 1

HCID 115508261-Propanone, 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-Yield 39%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

Then, 4.94 g of 1-[2,4-bis(methoxymethoxy)phenyl]-3-[3,4-bis(methoxymethoxy)phenyl]-1-propanone was dissolved in 48 ml of a hydrochloric acid/methanol reagent, and the solution was refluxed for 8 minutes and the reaction liquid was poured into ice water and extracted with ethyl acetate two times. The organic layer was washed with water three times, shaken with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the column chromatography (400 g of 230-400 mesh silica gel, n-hexane/ethyl acetate=3/2, 0.5 kg/cm2). Fractions of 50 ml were collected, and the 96th to 120th fractions were combined and the solvent was removed by distillation. The residue was recrystallized from n-hexane and chloroform to obtain 453.6 mg (yield=39.0%) of 1-(2,4-dihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-1-propanone.

Workup

  1. temperaturethe solution was refluxed for 8 minutes
  2. customthe reaction liquid
  3. extractionextracted with ethyl acetate two times
  4. washThe organic layer was washed with water three times
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed from the filtrate by distillation
  8. customFractions of 50 ml were collected
  9. customthe solvent was removed by distillation
  10. customThe residue was recrystallized from n-hexane and chloroform

Sources & evidence

ORD record
ord-8f840d01c9c846509a732b8961964fe5
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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