Water → 2-Hydroxy-3-(N,N-dibutylcarbamoylmethoxy)-3,3-diphenylpropionic acid

HRID 1635079Notes

Reaction equation

HRID 1635079 reaction equation
[OH:1][CH:2]([C:7]([O:20][CH2:21][C:22](=[O:32])[N:23]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5]C)=[O:4].[OH-].[Na+].O>O1CCOCC1>[OH:1][CH:2]([C:7]([O:20][CH2:21][C:22](=[O:32])[N:23]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH2:26][CH3:27])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18675624methyl 2-hydroxy-3-(N,N-dibutylcarbamoylmethoxy)-3,3-diphenylpropionate

Product 1

HCID 154275402-Hydroxy-3-(N,N-dibutylcarbamoylmethoxy)-3,3-diphenylpropionic acidYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

1.42 g of methyl 2-hydroxy-3-(N,N-dibutylcarbamoylmethoxy)-3,3-diphenylpropionate were dissolved in 10 ml of dioxane and 4.8 ml of 1N sodium hydroxide solution and stirred at room temperature for 3 hours. Water was then added to the mixture, and the aqueous phase was extracted with ether. The aqueous phase was acidified with hydrochloric acid and extracted with ethyl acetate, and the organic phase was dried over magnesium sulfate. After removal of the solvent by distillation, 1.1 g of oil were isolated and were immediately employed further.

Workup

  1. extractionthe aqueous phase was extracted with ether
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. customAfter removal of the solvent
  5. distillationby distillation

Sources & evidence

ORD record
ord-8a9e66e93f4b4cc993971a02d9a70cb8
Source dataset
uspto-grants-2003_01
Patent number
US06509341B1

Reaction notes

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