HCID 19744855, compound → HCID 11778945, compound

HRID 2254270Notes

Reaction equation

HRID 2254270 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8]COC)[CH:5]=[C:4]([O:12]COC)[C:3]=1[C:16](=[O:33])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]COC)=[C:21]([O:29]COC)[CH:20]=1.Cl.CO>CO>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:12])[C:3]=1[C:16](=[O:33])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]([OH:29])[CH:20]=1

Participants

4

Reactant 2

HCID 19744855HCID 19744855, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 11778945HCID 11778945, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 4.3 g of 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-[3,4-bis(methoxymethoxy)phenyl]-1-propanone was dissolved in 16 ml of methanol, and 33 ml of a hydrochloric acid/methanol reagent was added to the solution and the mixture was refluxed for 10 minutes. Then, the reaction liquid was poured into ice water and extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried with anhydrous sodium sulfate and filtered and the solvent was removed from the filtrate by distillation. The obtained residue was subjected to the silica gel column chromatography (160 g of 240-400 mesh silica gel, n-hexane/ethyl acetate=1/1, 0.3 kg/cm2). Fractions of 40 ml were collected and the 28th to 49th fractions were combined, and the solvent was removed by distillation to obtain 933.6 mg (yield=34.9%) of 1-(2,4,6-trihydroxyphenyl)-3-(3,4-dihydroxyphenyl)-1-propanone.

Workup

  1. temperaturethe mixture was refluxed for 10 minutes
  2. customThen, the reaction liquid
  3. extractionextracted with ethyl acetate
  4. washthe ethyl acetate layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed from the filtrate by distillation
  8. customFractions of 40 ml were collected
  9. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-63b2c60af0e8407188f33d4b032a28ec
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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