Hydrochloric Acid → 3-(4-Nitrophenoxy)propionic acid

HRID 493138Notes

Reaction equation

HRID 493138 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][CH2:13][C:14]([OH:16])=[O:15].[OH-].[K+].Cl>O.C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9804-NitrophenolHCID 78993-Chloropropionic acidHCID 14797Potassium Hydroxide

Product 1

HCID 3515353-(4-Nitrophenoxy)propionic acidYield 25%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-nitrophenol (14.0 g., 0.10 mol), 3-chloropropionic acid (10.8 g., 0.10 mol) and potassium hydroxide (11.2 g., 0.20 mol) in water and ethanol is heated at reflux temperature for 2 hours, cooled to ambient temperature, acidified with concentrated HCl to pH˜1, and extracted with ethyl acetate. The organic phase is washed with a saturated aqueous solution of sodium bicarbonate. The aqueous bicarbonate phase is acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The final ethyl acetate extract is washed with brine, dried over MgSO4 and concentrated in vacuo. The resultant residue is crystallized from ethyl ether and hexane to afford the title compound as an off-white crystalline solid, 5.3 g (25% yield), mp 117-118° C., identified by NMR and mass spectral analyses.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed with a saturated aqueous solution of sodium bicarbonate
  5. extractionextracted with ethyl acetate
  6. extractionThe final ethyl acetate extract
  7. washis washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe resultant residue is crystallized from ethyl ether and hexane

Sources & evidence

ORD record
ord-3601f0761b2943a09f09dde25a1fdd58
Source dataset
uspto-grants-2009_05
Patent number
US07534801B2

Reaction notes

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