Hydrochloric Acid → HCID 14368086, compound

HRID 1030721Notes

Reaction equation

HRID 1030721 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-cda6235b3e83438bba18f7e8b9c726dc
Source dataset
uspto-grants-1992_04
Patent number
US05106871

Reaction notes

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