Sodium Bicarbonate → HCID 54388297, compound

HRID 2254255Notes

Reaction equation

HRID 2254255 reaction equation
[C:1]([O:4][C:5]1[C:24]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])=[C:23]([O:30]COC)[CH:22]=[C:21]([O:34]COC)[C:6]=1[C:7](=[O:20])[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]COC)=[CH:12][CH:11]=1)(=[O:3])[CH3:2].Cl.CO.C(=O)([O-])O.[Na+]>>[C:1]([O:4][C:5]1[C:24]([CH2:25][CH:26]=[C:27]([CH3:28])[CH3:29])=[C:23]([OH:30])[CH:22]=[C:21]([OH:34])[C:6]=1[C:7](=[O:20])[CH:8]=[CH:9][C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 54335119HCID 54335119, compound

Product 1

HCID 54388297HCID 54388297, compoundYield 54.4%

Procedure

Then, a liquid mixture of 4.95 g of 2'-acetoxy-4,4',6'-tris(methoxymethoxy)-3'-(3-methyl-2-butenyl)chalcone and 8 ml of a hydrochloric acid/methanol reagent was heated and refluxed for 10 minutes, and the temperature of the reaction mixture was lowered to room temperature and the reaction mixture was neutralized with an aqueous solution of sodium hydrogencarbonate and extracted with 1 l of ethyl acetate. The ethyl layer was 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 (130 g of 230-400 mesh silica gel, n-hexane/ethyl acetate=3/1, 0.3 kg/cm2). Fractions of 100 ml were collected and the 13th to 26th fractions were combined to obtain 2.0 g (yield=54.3%) of 2'-acetoxy-4,4',6'-trihydroxy-3'-(3-methyl-2-butenyl)chalcone in the form of a yellow powder.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 10 minutes
  3. customwas lowered to room temperature
  4. extractionextracted with 1 l of ethyl acetate
  5. washThe ethyl layer was washed 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

Sources & evidence

ORD record
ord-b310ab52685f46a0a8747520cbf8eb50
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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