Sodium Bicarbonate → HCID 19744862, compound

HRID 1030752Notes

Reaction equation

HRID 1030752 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([O:13]COC)[CH:5]=[C:4]([O:17]COC)[C:3]=1[C:21](=[O:34])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30]COC)=[CH:26][CH:25]=1.Cl.CO.C(=O)([O-])O.[Na+]>CO>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:11])[CH3:12])=[C:6]([OH:13])[CH:5]=[C:4]([OH:17])[C:3]=1[C:21](=[O:34])[CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([OH:30])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 19744883HCID 19744883, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 19744862HCID 19744862, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 2.55 g of the so-obtained 1-[2-hydroxy-4,6-bis(methoxymethoxy)-3-isopentylphenyl]-3-(4-methoxymethoxyphenyl)-1-propanone was dissolved in 2 ml of methanol, and 4 ml of a hydrochloric acid/methanol reagent was added to the solution and the mixture was heated and refluxed for 20 minutes. The temperature of the reaction mixture was lowered to room temperature, and the reaction mixture was neutralized with a saturated solution of sodium hydrogencarbonate and extracted with 500 ml of ethyl acetate. The ethyl acetate layer was washed with water (200 ml×4 times), shaken with a saturated aqueous solution of sodium chloride (200 ml×2 times), dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation, and the residue was recrystallized from a mixed solvent of chloroform and methanol to obtain 1.3 g (yield=70.7%) of 1-(2,4,6-trihydroxy-3-isopentylphenyl)-3-(4-hydroxyphenyl)-1-propanone in the form of a yellow prism.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 20 minutes
  3. customwas lowered to room temperature
  4. extractionextracted with 500 ml of ethyl acetate
  5. washThe ethyl acetate layer was washed with water (200 ml×4 times)
  6. dry with materialdried with anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed from the filtrate by distillation
  9. customthe residue was recrystallized from a mixed solvent of chloroform and methanol

Sources & evidence

ORD record
ord-8f307f0ddc644a22872b711c508ffef5
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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