Hydrochloric Acid → HCID 57032532, compound

HRID 2254248Notes

Reaction equation

HRID 2254248 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=O)[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[C:5]([O:23][CH2:24][C:25]([O:27]C)=[O:26])[C:4]=1[CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32].[OH-:34].[K+].Cl>CO>[C:25]([CH2:24][O:23][C:5]1[C:4]([CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[C:6]=1[CH2:11][C:12](=[O:34])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)([OH:27])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19744904HCID 19744904, compound

Product 1

HCID 57032532HCID 57032532, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 1.9 g of 1-[4,6-dimethoxy-2-methoxycarbonylmethoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-methoxyphenyl)-1-propanone was dissolved in 20 ml of methanol, and 20 ml of a 5% aqueous solution of potassium hydroxide was added to the solution and the mixture was stirred at room temperature for 30 minutes to effect a reaction. After the reaction, the reaction mixture was made acidic by dilute hydrochloric acid, extracted with diethyl ether and filtered, and the solvent was removed from the filtrate by distillation. The obtained residue was recrystallized from a mixed solvent of ethyl acetate and diethyl ether to obtain 1.7 g (yield=92.4%) of 1-[2-carboxymethoxy-4,6-dimethoxy-3-(3-methyl-2-butenyl)phenyl]-3-(4-methoxyphenyl)-propanone in the form of a colorless prism.

Workup

  1. customa reaction
  2. customAfter the reaction
  3. extractionextracted with diethyl ether
  4. filtrationfiltered
  5. customthe solvent was removed from the filtrate by distillation
  6. customThe obtained residue was recrystallized from a mixed solvent of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-08569680a1114a76ace31f9ae6a32bfd
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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