Hydrochloric Acid → HCID 14368084, compound

HRID 2254229Notes

Reaction equation

HRID 2254229 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]([OH:20])=[C:16]([O:21][CH3:22])[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]([OH:20])=[C:16]([O:21][CH3:22])[CH:15]=1)([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 14368070HCID 14368070, compound

Product 1

HCID 14368084HCID 14368084, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 12.0 g of 1-(4,6-dimethoxy-2-methoxycarbonylmethoxy-3-isopentylphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-propanone was dissolved in 120 ml of methanol, and 70 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 addition of dilute hydrochloric acid, and the solvent was removed by distillation and the residue was crystallized from ethyl acetate/diethyl ether/hexane to obtain 9.7 g (yield=85% of 1-(2-carboxymethoxy-4,6-dimethoxy-3-isopentylphenyl)-3-(4-hydroxy-3-methoxyphenyl)-1-propanone in the form of a white solid.

Workup

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

Sources & evidence

ORD record
ord-de4ed49151a54266a05d65c53b12574a
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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