Acetic Acid → 3-(2-Nitrophenyl)propionic acid

HRID 647309Notes

Reaction equation

HRID 647309 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11](C(OCC)=O)[C:12]([O:14]CC)=[O:13])([O-:3])=[O:2].C(O)(=O)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]([OH:14])=[O:13])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 309274Diethyl 2-(2-(hydroxy(oxido)amino)benzyl)malonate

Product 1

HCID 748183-(2-Nitrophenyl)propionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The 164.2 g of oil containing diethyl (2-nitrophenylmethyl)-1,3-propanedioate, from Step A, was combined with 1 L of acetic acid and 1 L of aqueous 20% hydrochloric acid, and heated under reflux for 16 hours. The reaction mixture was cooled to ambient temperature, and concentrated under reduced pressure to give a residue. The residue was stirred with 450 mL of water, then 450 mL of aqueous 10% sodium hydroxide solution was added. The mixture was stirred for one hour, then was extracted with four portions of 450 mL each of diethyl ether. The organic layer was discarded. The aqueous layer was acidified with hydrochloric acid, and extracted with three portions of 300 mL each of diethyl ether. The combined extracts were dried with sodium sulfate, filtered, and the filtrate concentrated under reduced pressure to give a solid residue. The solid was dissolved with heating in 200 mL of toluene, and the solution was stirred for 16 hours while cooling to ambient temperature. The resultant slurry was further cooled to 10° C., and the solid collected by filtration. The solid was washed with pentane to give 74.2 g of 3-(2-nitrophenyl)propionic acid, m.p. 111°-112° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. concentrationconcentrated under reduced pressure
  4. customto give a residue
  5. extractionwas extracted with four portions of 450 mL each of diethyl ether
  6. extractionextracted with three portions of 300 mL each of diethyl ether
  7. dry with materialThe combined extracts were dried with sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated under reduced pressure
  10. customto give a solid residue
  11. dissolutionThe solid was dissolved
  12. stirringthe solution was stirred for 16 hours
  13. temperaturewhile cooling to ambient temperature
  14. temperatureThe resultant slurry was further cooled to 10° C.
  15. filtrationthe solid collected by filtration
  16. washThe solid was washed with pentane

Sources & evidence

ORD record
ord-702379ee7b934d57bdfa612c7cda4d4a
Source dataset
uspto-grants-1983_10
Patent number
US04408057

Reaction notes

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