Sodium Bicarbonate → HCID 14368081, compound

HRID 2254216Notes

Reaction equation

HRID 2254216 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:36])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30]COC)=[C:26]([O:34][CH3:35])[CH:25]=1.Cl.CO.C(=O)([O-])O.[Na+]>CO>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[C:6]([OH:13])[CH:5]=[C:4]([OH:17])[C:3]=1[C:21](=[O:36])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([O:34][CH3:35])[CH:25]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 14368062HCID 14368062, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 14368081HCID 14368081, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 5.0 g of 1-[2-hydroxy-4,6-bis(methoxymethoxy)-3-isopentylphenyl]-3-(3-methoxy-4-methoxymethoxyphenyl)-1-propanone was dissolved in 12.0 ml of methanol, and 37 ml of a hydrochloric acid/methanol reagent was added to the solution and the mixture was refluxed for 1 hour. The reaction liquid was neutralized with a saturated solution of sodium hydrogencarbonate and extracted with diethyl ether. The ether layer was washed with water, dried with anhydrous magnesium sulfate, and concentrated under a reduced pressure. The reaction mixture was subjected to the column chromatography [230-400 mesh Kieselgel 60; eluting solvent=chloroform/methanol (30/1)] to obtain 1.9 g (yield=50.9%) of 1-(2,4,6-trihydroxy-3-isopentylphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-propanone.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customThe reaction liquid
  3. extractionextracted with diethyl ether
  4. washThe ether layer was washed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-2417a53e036245978335c47c389e72aa
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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