Sodium Bicarbonate → HCID 19744893, compound

HRID 2254274Notes

Reaction equation

HRID 2254274 reaction equation
[CH3:1][O:2][C:3]([CH2:5][O:6][C:7]1[C:12]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])=[C:11]([O:18]COC)[CH:10]=[C:9]([O:22]COC)[C:8]=1[C:26](=[O:39])[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35]COC)=[CH:31][CH:30]=1)=[O:4].Cl.CO.C(=O)([O-])O.[Na+]>CO>[OH:18][C:11]1[CH:10]=[C:9]([OH:22])[C:8]([C:26](=[O:39])[CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=2)=[C:7]([O:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])[C:12]=1[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 19744871HCID 19744871, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 19744893HCID 19744893, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 1.30 g of 1-[2-methoxycarbonylmethoxy-4,6-bis(methoxymethoxy)-3-isopentylphenyl]-3-(4-methoxymethoxyphenyl)-1-propanone was dissolved in 3 ml of methanol, and 10 ml of a hydrochloric acid/methanol reagent was added to the solution and the mixture was heated and refluxed for 40 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 hydrogencarbonate and extracted with 500 ml of ethyl acetate. The ethyl acetate 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. The obtained residue was recrystallized from chloroform to obtain 918 mg (yield=93.0%) of 1-(4,6-dihydroxy-2-methoxycarbonylmethoxy-3-isopentylphenyl)-3-(4-hydroxyphenyl)-1-propanone in the form of a colorless prism.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 40 minutes
  3. customwas lowered to room temperature
  4. extractionextracted with 500 ml of ethyl acetate
  5. washThe ethyl acetate 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. customThe obtained residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-79abe922c4c349cbb05a4647bee71ec4
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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