Sodium Hydroxide → 2-(4-Nitrophenyl)propionic acid

HRID 2413908Notes

Reaction equation

HRID 2413908 reaction equation
[CH3:1][C:2]([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)(C(OCC)=O)[C:3]([O:5]CC)=[O:4].[OH-].[Na+]>C(O)C.O>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12380744Diethyl methyl(4-nitrophenyl)propanedioate

Product 1

HCID 892442-(4-Nitrophenyl)propionic acidYield 68.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

147 g of the crude diethyl 2-methyl-2-(4-nitrophenyl)-malonate was dissolved in 600 ml of ethanol, and to this was added a solution of 42.4 g (0.846 mole) of 93% sodium hydroxide in 400 ml of water and the solution was reacted at 50° C. for 3 hours. After that, to the reaction mixture was added 1 l of water and the formed oily substance and an aqueous layer were separated. The aqueous layer was acidified with conc. hydrochloric acid and was extracted with 700 ml of ethyl acetate. The ethyl acetate layer was washed with a saturated solution of sodium chloride and dried over anhydrous magnesium sulfate. After filtering out magnesium sulfate, ethyl acetate was distilled off to give 66.8 g of crude 2-(4-nitrophenyl)propionic acid.

Workup

  1. customthe solution was reacted at 50° C. for 3 hours
  2. customthe formed oily substance and an aqueous layer were separated
  3. extractionwas extracted with 700 ml of ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering out magnesium sulfate, ethyl acetate
  7. distillationwas distilled off

Sources & evidence

ORD record
ord-ebc26e7989a84217bf46f5446e02ca5f
Source dataset
uspto-grants-1988_01
Patent number
US04720506

Reaction notes

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