Hydrochloric Acid → HCID 19744872, compound

HRID 1030751Notes

Reaction equation

HRID 1030751 reaction equation
C([O:4][C:5]1[C:10]([CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[C:9]([OH:16])[CH:8]=[C:7]([OH:17])[C:6]=1[C:18](=[O:28])[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)(=O)C.[OH-].[K+].Cl>CO>[OH:4][C:5]1[C:10]([CH2:11][CH:12]=[C:13]([CH3:14])[CH3:15])=[C:9]([OH:16])[CH:8]=[C:7]([OH:17])[C:6]=1[C:18](=[O:28])[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19744899HCID 19744899, compound

Product 1

HCID 19744872HCID 19744872, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 10 ml of a methanol solution of 500 mg of the 1-[2-acetoxy-4,6-dihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-1-propanone obtained in Specific Example 24 was added an aqueous solution of potassium hydroxide (1.5 g/5 ml), and the mixture was stirred at room temperature for 45 minutes. After the reaction, the reaction mixture was carefully neutralized wit dilute hydrochloric acid, extracted with 300 ml of ethyl acetate, washed with water (100 ml×4 times), shaken with a saturated aqueous solution of sodium chloride (100 ml×2 times), dried with anhydrous sodium sulfate and filtered. The solvent was removed from the filtrate by distillation, and the obtained residue was recrystallized from a mixed solvent of chloroform and methanol to obtain 325 mg (yield=73.0%) of 1-[2,4,6-trihydroxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-hydroxyphenyl)-1-propanone in the form of a colorless prism.

Workup

  1. customAfter the reaction
  2. extractionextracted with 300 ml of ethyl acetate
  3. washwashed with water (100 ml×4 times)
  4. stirringshaken with a saturated aqueous solution of sodium chloride (100 ml×2 times)
  5. dry with materialdried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed from the filtrate by distillation
  8. customthe obtained residue was recrystallized from a mixed solvent of chloroform and methanol

Sources & evidence

ORD record
ord-eb1b5f79437e4da3affc17ba72faa561
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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