HCID 19744854, compound → HCID 19744876, compound

HRID 1030765Notes

Reaction equation

HRID 1030765 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:39])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30]COC)=[C:26]([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH:25]=1.Cl.CO>CO>[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]([CH3:11])[CH3:12])=[C:6]([OH:13])[CH:5]=[C:4]([OH:17])[C:3]=1[C:21](=[O:39])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([CH2:34][CH2:35][CH:36]([CH3:38])[CH3:37])[CH:25]=1

Participants

4

Reactant 2

HCID 19744854HCID 19744854, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 19744876HCID 19744876, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 7.00 g of 1-[2-hydroxy-4,6-bis(methoxymethoxy)-3-isopentylphenyl]-3-(3-isopentyl-4-methoxymethoxyphenyl)-1-propanone was dissolved in 17.5 ml of methanol, and 52.0 ml of a hydrochloric acid/methanol reagent was added to the solution and the mixture was refluxed for 30 minutes. The reaction liquid was poured into ice water and extracted with ethyl acetate, and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride in sequence and dried with anhydrous sodium sulfate. The solvent was removed by distillation and the obtained residue was recrystallized from chloroform to obtain 3.84 g (yield=72.4%) of 1-(2,4,6-trihydroxy-3-isopentylphenyl)-3-(4-hydroxy-3-isopentylphenyl)-1-propanone.

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. customThe reaction liquid
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water
  5. dry with materiala saturated aqueous solution of sodium chloride in sequence and dried with anhydrous sodium sulfate
  6. customThe solvent was removed by distillation
  7. customthe obtained residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-aba5147e456a44538af274732cbd4d50
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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