Sodium Hydroxide → 3-[2,4-Dimethoxy-5-(4-methoxybenzoyl)phenyl]propionic acid

HRID 893418Notes

Reaction equation

HRID 893418 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=[O:20])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][C:4]=1[CH2:21][CH2:22][C:23]([O:25]C)=[O:24].[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[C:6]([C:11](=[O:20])[C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)=[CH:5][C:4]=1[CH2:21][CH2:22][C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14460995Methyl 3-[2,4-dimethoxy-5-(4-methoxybenzoyl)phenyl]propionate

Product 1

HCID 144609963-[2,4-Dimethoxy-5-(4-methoxybenzoyl)phenyl]propionic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

60.9 g of methyl 3-[2,4-dimethoxy-5-(4-methoxybenzoyl)phenyl]propionate are mixed with 300 ml of 2N sodium hydroxide solution and 300 ml of dioxane and stirred overnight. The dioxane is then removed in vacuo, and the alkaline aqueous solution is extracted once with 100 ml of ethyl acetate. The aqueous phase is adjusted to pH 2 with concentrated hydrochloric acid, when part of the product separates out. The mixture is extracted three times with 200 ml of ethyl acetate each time, and the organic phase is washed with water, dried over sodium sulfate and concentrated. The residue is recrystallized from ethyl acetate/acetone/hexane.

Workup

  1. customThe dioxane is then removed in vacuo
  2. extractionthe alkaline aqueous solution is extracted once with 100 ml of ethyl acetate
  3. extractionThe mixture is extracted three times with 200 ml of ethyl acetate each time
  4. washthe organic phase is washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is recrystallized from ethyl acetate/acetone/hexane

Sources & evidence

ORD record
ord-c243e0a9001f4ea59539d42c52d1062f
Source dataset
uspto-grants-1992_06
Patent number
US05124478

Reaction notes

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