Hydrochloric Acid → HCID 14368085, compound

HRID 2254233Notes

Reaction equation

HRID 2254233 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=[O:23])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([OH:22])[CH:15]=2)=[C:5]([O:24][CH2:25][C:26]([O:28]C)=[O:27])[C:4]=1[CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33].[OH-].[K+].Cl>CO>[C:26]([CH2:25][O:24][C:5]1[C:4]([CH2:30][CH2:31][CH:32]([CH3:33])[CH3:34])=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[C:6]=1[C:11](=[O:23])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([OH:22])[CH:15]=1)([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14368073HCID 14368073, compound

Product 1

HCID 14368085HCID 14368085, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 3.0 g of 1-(4,6-dimethoxy-2-methoxycarbonylmethoxy-3-isopentylphenyl)-3-(3-hydroxy-4-methoxyphenyl)-1-propanone was dissolved in 30 ml of methanol, and 18 ml of a 5% aqueous solution of potassium hydroxide was added to the solution and the mixture was stirred at room temperature for 20 minutes. Then, the reaction mixture was made weakly acidic by an addition of dilute hydrochloric acid, the solvent was removed from the mixture by distillation, and the residue was crystallized from ethyl acetate/diethyl ether/hexane to obtain 2.6 g (yield=90%) of 1-(2-carboxymethoxy-4,6-dimethoxy-3-isopentylphenyl)-3-(3-hydroxy-4-methoxyphenyl)-1-propanone in the form of a colorless transparent plate.

Workup

  1. customthe solvent was removed from the mixture by distillation
  2. customthe residue was crystallized from ethyl acetate/diethyl ether/hexane

Sources & evidence

ORD record
ord-3a96bf81d63e4c809ac7ef448c3ef054
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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