Sodium Bicarbonate → HCID 72752070, compound

HRID 2254260Notes

Reaction equation

HRID 2254260 reaction equation
[OH:1][C:2]1[C:21]([CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])=[C:20]([O:27]COC)[CH:19]=[C:18]([O:31]COC)[C:3]=1[C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]COC)=[CH:9][CH:8]=1.Cl.CO.C(=O)(O)[O-].[Na+]>>[OH:1][C:2]1[C:21]([CH2:22][CH2:23][CH:24]([CH3:25])[CH3:26])=[C:20]([OH:27])[CH:19]=[C:18]([OH:31])[C:3]=1[C:4](=[O:17])[CH:5]=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 54214259HCID 54214259, compound

Product 1

HCID 72752070HCID 72752070, compoundYield 59.3%

Procedure

Then, a liquid mixture of 1.45 g of 2'-hydroxy-4,4',6'-tris(methoxymethoxy)-3'-isopentylchalcone and 4 ml of a hydrochloric acid/methanol reagent was heated and refluxed for 10 minutes. The temperature of the reaction mixture was lowered to room temperature, and the reaction mixture was neutralized with a saturated aqueous solution of sodium bicarbonate, extracted with 500 ml of ethyl acetate, washed with water, shaken with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation and the obtained residue was subjected to the silica gel column chromatography (diameter=4.5 cm, 130 g of silica gel, 9.3 kg/cm2) using a mixed solvent of n-hexane and ethyl acetate (n-hexane/ethyl acetate=3/1). Fractions of 100 ml were collected, and the 42nd to 56th fractions were combined, and the solvent was removed by distillation and the residue was recrystallized from a mixed solvent of chloroform and methanol to obtain 620 mg (yield=59.3%) of 2' ,4,4',6'-tetrahydroxy-3'-isopentylchalcone in the form of a yellow prism.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 10 minutes
  3. customwas lowered to room temperature
  4. extractionextracted with 500 ml of ethyl acetate
  5. washwashed with water
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate by distillation
  9. customFractions of 100 ml were collected
  10. customthe solvent was removed by distillation
  11. customthe residue was recrystallized from a mixed solvent of chloroform and methanol

Sources & evidence

ORD record
ord-27e492b5aed2409fb16b1b52f89d46be
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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