Sodium Bicarbonate → HCID 19744893, compound

HRID 1030759Notes

Reaction equation

HRID 1030759 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-52f604eef12248c0ad634a8d7e39a9ac
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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