Hydrochloric Acid → HCID 19744870, compound

HRID 2254222Notes

Reaction equation

HRID 2254222 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:20])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:5]([O:21][CH2:22][C:23]([O:25]C)=[O:24])[C:4]=1[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30].[OH-].[K+].Cl>CO>[C:23]([CH2:22][O:21][C:5]1[C:4]([CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[C:9](=[O:20])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 19744863HCID 19744863, compound

Product 1

HCID 19744870HCID 19744870, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Then, 14.2 g of 1-(4-methoxy-2-methoxycarbonylmethoxy-3-isopentylphenyl)-3-(4-methoxyphenyl)-1-propanone was dissolved in 80 ml of methanol, and 100 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. After the reaction, the reaction mixture was made acidic by dilute hydrochloric acid and extracted with diethyl ether. The solvent was removed from the diethyl ether layer by distillation to obtain 13.1 g (yield=95.3%) of 1-(carboxymethoxy-4-methoxy-3-isopentylphenyl)-3-(4-methoxyphenyl)-1-propanone in the form of a colorless oil.

Workup

  1. customAfter the reaction
  2. extractionextracted with diethyl ether
  3. customThe solvent was removed from the diethyl ether layer by distillation

Sources & evidence

ORD record
ord-d502d243b90646309d2f20f03f5a58ec
Source dataset
uspto-grants-1993_08
Patent number
US05234951

Reaction notes

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