Sodium Bicarbonate → HCID 53766578, compound

HRID 1030738Notes

Reaction equation

HRID 1030738 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]([CH:25]=[CH:26][CH: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 53766578HCID 53766578, compoundYield 54.4%

Procedure

Then, a liquid mixture of 4.95 g of 2'-acetoxy4,4',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 hydrogen-carbonate 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-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-e276760c4a5c41bda216ab4816061074
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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