HCID 19744867, compound → HCID 14368087, compound

HRID 1030725Notes

Reaction equation

HRID 1030725 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11]COC)[CH:5]=[C:4]([O:15]COC)[C:3]=1[C:19](=[O:32])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28]COC)=[CH:24][CH:23]=1.Cl.CO>CO>[OH:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][CH2:20][C:19]([C:3]2[C:4]([OH:15])=[CH:5][C:6]([OH:11])=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=2[OH:1])=[O:32])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 19744867HCID 19744867, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 14368087HCID 14368087, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 20.9 g of 1-[2-hydroxy-4,6-bis(methoxymethoxy)-3-n-propylphenyl]-3-(4-methoxymethoxyphenyl)-1-propanone was dissolved in 40 ml of methanol, and 20 ml of a 5-15% hydrochloric acid/methanol reagent was added to the solution and the mixture was heated and refluxed for 2 hours. The temperature was lowered to room temperature, 200 ml of a saturated aqueous solution of sodium bicarbonate, and the mixture was extracted with ethyl acetate. The solvent was removed from the ethyl acetate layer by distillation and the obtained residue was subjected to the polyamide column chromatography (diluting solvent=methanol) and recrystallized from benzene to obtain 10.2 g (yield=69.1%) of 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-n-propylphenyl)-1-propanone in the form of a yellow prism.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 2 hours
  3. customwas lowered to room temperature
  4. extraction200 ml of a saturated aqueous solution of sodium bicarbonate, and the mixture was extracted with ethyl acetate
  5. customThe solvent was removed from the ethyl acetate layer by distillation
  6. additionthe obtained residue was subjected to the polyamide column chromatography (diluting solvent=methanol)
  7. customrecrystallized from benzene

Sources & evidence

ORD record
ord-9fdb778e6d634aad965782b7ccc4780f
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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