HCID 19744889, compound → HCID 14368082, compound

HRID 2254218Notes

Reaction equation

HRID 2254218 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:38])[CH2:22][CH2:23][C:24]1[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32]COC)=[C:26]([O:36][CH3:37])[CH:25]=1.Cl.CO>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:38])[CH2:22][CH2:23][C:24]1[CH:25]=[C:26]([O:36][CH3:37])[C:27]([OH:32])=[C:28]([O:30][CH3:31])[CH:29]=1

Participants

4

Reactant 2

HCID 19744889HCID 19744889, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 14368082HCID 14368082, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, 10.0 g of 1-[2-hydroxy-4,6-bis(methoxymethoxy)-3-isopentylphenyl]-3-(3,5-dimethoxy-4-methoxymethoxyphenyl)-1-propanone was dissolved in 25.0 ml of methanol, and 70 ml of a hydrochloric acid-methanol reagent was added to the solution and the mixture was refluxed in an argon atmosphere for 1 hour. The reaction liquid was concentrated under a reduced pressure and subjected to the column chromatography [230-400 mesh Kieselgel 60; eluting solvent=chloroform/methanol (20/1)] to obtain 2.7 g (yield=36.8%) of yellowish brown 1-(2,4,6-trihydroxy-3-isopentylphenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone.

Workup

  1. temperaturethe mixture was refluxed in an argon atmosphere for 1 hour
  2. customThe reaction liquid
  3. concentrationwas concentrated under a reduced pressure

Sources & evidence

ORD record
ord-8a391307009e4ed182b707bff52af311
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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