Sodium Bicarbonate → Davidigenin

HRID 1030746

Reaction equation

COC[O:4][C:5]1[CH:10]=[C:9]([O:11]COC)[CH:8]=[CH:7][C:6]=1[C:15](=[O:28])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24]COC)=[CH:20][CH:19]=1.Cl.CO.C(=O)([O-])O.[Na+].CCCCCC.C(OCC)(=O)C>CO>[OH:4][C:5]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:6]=1[C:15](=[O:28])[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Then, 4.44 g of the so-obtained 1-[2,4-bis(methoxymethoxy)phenyl]-3-(4-methoxymethoxyphenyl)-1-propanone was dissolved in methanol, and 38 ml of a hydrochloric acid/methanol reagent was added to the solution and the mixture was stirred at 60° C. for 30 minutes. After the reaction, the reaction liquid was poured into ice water, neutralized with a saturated solution of sodium hydrogencarbonate and extracted with ethyl acetate, and the organic layer was washed with water, dried with sodium sulfate and concentrated under a reduced pressure to obtain a reaction mixture The reaction mixture was subjected to the column chromatography [69 g of 270-400 mesh Kieselgel 60; 0.5 kg/cm2 ; eluting solvent=hexane/ethyl acetate (1/1)] to obtain 2.55 g (yield=86.7%) of 1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone.

Workup

customAfter the reaction
customthe reaction liquid
extractionextracted with ethyl acetate
washthe organic layer was washed with water
dry with materialdried with sodium sulfate
concentrationconcentrated under a reduced pressure
customto obtain a reaction mixture The reaction mixture

Sources & evidence

ORD record: ord-bcedcc4a170d49d18df8ada287fc3751
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05106871

Linked notes

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