Hydrochloric Acid → (4-Nitrophenoxy)acetic acid

HRID 1910750Notes

Reaction equation

HRID 1910750 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH2:14][C:15]([OH:17])=[O:16].Cl>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:14][C:15]([OH:17])=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9804-NitrophenolHCID 6227Bromoacetic AcidHCID 24758Sodium hydride

Product 1

HCID 15720(4-Nitrophenoxy)acetic acidYield 49.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-nitro-phenol (5.0 g, 36 mmol) was added to a stirred suspension of sodium hydride (3.13 g; 55% in mineral oil; 71.9 mmol) in dry tetrahydrofuran (100 mL) and stirred for 30 min at ambient temperature. Bromoacetic acid (6.0 g, 43.2 mmol) was added and the mixture then heated at reflux overnight. The reaction mixture was cooled to ambient temperature, neutralised with dilute hydrochloric acid and extracted with ethyl acetate. The separated organic layer was extracted with sodium bicarbonate solution and the aqueous solution was acidified with concentrated HCl to pH ˜3 to afford a white precipitate, which was filtered and dried under vacuum to give (4-nitro-phenoxy)-acetic acid (3.5 g, 45%).

Workup

  1. temperaturethe mixture then heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled to ambient temperature
  4. extractionextracted with ethyl acetate
  5. extractionThe separated organic layer was extracted with sodium bicarbonate solution
  6. customto afford a white precipitate, which
  7. filtrationwas filtered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-e45f720fb04247a9b4da655cce13a508
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

Loading…