Sodium Hydroxide → 2-[1-(2,4-Dimethoxyphenyl)hexyl]malonic acid

HRID 1418171Notes

Reaction equation

HRID 1418171 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]([CH:19]([C:25]([O:27]CC)=[O:26])[C:20]([O:22]CC)=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>O.C(O)C>[CH3:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:6]=1[CH:13]([CH:19]([C:20]([OH:22])=[O:21])[C:25]([OH:27])=[O:26])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19348766Diethyl 2-[1-(2,4-dimethoxyphenyl)hexyl]malonate

Product 1

HCID 193484652-[1-(2,4-Dimethoxyphenyl)hexyl]malonic acidYield 92.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 4.40 g (110 mmol) of sodium hydroxide in 14 ml of water was added to a solution of 8.37 g (22.0 mmol) of diethyl 2-[1-(2,4-dimethoxy-phenyl)hexyl]malonate (prepared as described in Preparation 2) in 50ml of ethanol, and the resulting mixture was heated under reflux for 2.5 hours. At the end of this time, the reaction mixture was allowed to cool to room temperature, after which it was freed from ethanol by evaporation under reduced pressure. The resulting residue was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water and then with a. saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, to give 6.57 g of the title compound as a foam-like substance.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. customafter which it was freed from ethanol by evaporation under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialsaturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-4c4e191e1eb44d6b90b69a203a796c83
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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