HCID 14672109, compound → 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one

HRID 1030749Notes

Reaction equation

HRID 1030749 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([O:8]COC)[CH:5]=[C:4]([O:12]COC)[C:3]=1[C:16](=[O:29])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]COC)=[CH:21][CH:20]=1.Cl.C(O)C>CO>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([OH:12])[C:3]=1[C:16](=[O:29])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 14672109HCID 14672109, compoundHCID 21887872Ethanol hydrochloride

Product 1

HCID 47883-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-oneYield 64.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 5.94 g of 1-[2-hydroxy-4,6-bis(methoxymethoxy)phenyl]-3-(4-methoxymethoxyphenyl)-1-propanone was stirred with 87 ml of methanol and 52 ml of a hydrochloric acid/ethanol reagent at 60° C. for 35 minutes. Then, the reaction mixture was poured into ice water and the precipitated crystal was recovered by filtration and dried. The crystal was subjected to the column chromatography [330 g of 270-400 mesh Kieselgel 60; 0.5 kg/cm2 ; eluting solvent=hexane/ethyl acetate (2/1)]. Fractions of 50 ml were collected and the 11th to 42nd fractions were combined to obtain 2.58 g (yield=64.4%) of 1-(2,4,6-trihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone.

Workup

  1. filtrationthe precipitated crystal was recovered by filtration
  2. customdried
  3. customFractions of 50 ml were collected

Sources & evidence

ORD record
ord-ce76dbeb89af41a1a4a046d058e2387d
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

Loading…