Hydrochloric Acid → HCID 14368086, compound

HRID 2254237Notes

Reaction equation

HRID 2254237 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=[O:25])[CH2:12][CH2:13][C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([OH:22])=[C:16]([O:23][CH3:24])[CH:15]=2)=[C:5]([O:26][CH2:27][C:28]([O:30]C)=[O:29])[C:4]=1[CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35].[OH-].[K+].Cl>CO>[C:28]([CH2:27][O:26][C:5]1[C:4]([CH2:32][CH2:33][CH:34]([CH3:35])[CH3:36])=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[C:6]=1[C:11](=[O:25])[CH2:12][CH2:13][C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([OH:22])=[C:16]([O:23][CH3:24])[CH:15]=1)([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14368076HCID 14368076, compound

Product 1

HCID 14368086HCID 14368086, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 1.5 g of 1-(4,6-dimethoxy-2-methoxycarbonylmethoxy-3-isopentylphenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone was dissolved in 15 ml of methanol, and 8.6 ml of a 5% 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 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 1.0 g (yield=68%) of 1-(2-carboxymethoxy-4,6-dimethoxy-3-isopentylphenyl)-3-(4-hydroxy-3,5-dimethoxyphenyl)-1-propanone in the form of a white cotton-like crystal.

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-ec8b12830ee04b5ca11dfffc8e20a356
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

Loading…