Methanol → 2a(2),4a(2),6a(2),3,4-Pentahydroxychalcone

HRID 2254258Notes

Reaction equation

CO.[OH:3][C:4]1[CH:27]=[C:26]([O:28]COC)[CH:25]=[C:24]([O:32]COC)[C:5]=1[C:6](=[O:23])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]COC)=[C:11]([O:19]COC)[CH:10]=1.Cl.CO>O>[OH:3][C:4]1[CH:27]=[C:26]([OH:28])[CH:25]=[C:24]([OH:32])[C:5]=1[C:6](=[O:23])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:19])[CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Then, 20 ml of methanol was added to 5.19 g of the so-obtained 2'-hydroxy-3,4,4',6'-tetrakis(methoxymethoxy)chalcone, and 40 ml of a hydrochloric acid/methanol reagent was added to the formed suspension and the mixture was stirred at 60° C. for 15 minutes. After the reaction, the reaction liquid was poured into water, and the precipitated crystal was recovered by filtration, washed with water and dried to obtain 2.81 g (yield=87.2%) of a crude crystal. The crude crystal was subjected to the column chromatography (200 g of 240-400 mesh Kieselgel 60; 0.3 kg/cm2 : eluting solvent: hexane/ethyl acetate=2/1, 2700 ml, hexane/ethyl acetate=1/1). Fractions of 50 ml were collected and the 92nd to 149th fractions were combined and concentrated to dryness to obtain 1.06 g (yield=32.9%) of 2',3,4,4',6'-pentahydroxychalcone.

Workup

additionwas added to the formed suspension
customAfter the reaction
customthe reaction liquid
filtrationthe precipitated crystal was recovered by filtration
washwashed with water
customdried
customto obtain 2.81 g (yield=87.2%) of a crude crystal
washThe crude crystal was subjected to the column chromatography (200 g of 240-400 mesh Kieselgel 60; 0.3 kg/cm2 : eluting solvent: hexane/ethyl acetate=2/1, 2700 ml, hexane/ethyl acetate=1/1)
customFractions of 50 ml were collected
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-5f9a2bb56f7c49fda1dc686d9b508743
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05234951

Reaction notes

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