Hydrochloric Acid → 4-Hydroxy-3-nitrophenylacetic acid

HRID 1264621Notes

Reaction equation

HRID 1264621 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C)=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[OH-].[Na+].Cl>O.CO>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1473109Methyl 2-(4-hydroxy-3-nitrophenyl)acetate

Product 1

HCID 4473644-Hydroxy-3-nitrophenylacetic acidYield 99.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

Methyl 4-hydroxy-3-nitrophenylacetate (21.1 g, 0.1 mol) was suspended in a mixture of water (55 ml) and methanol (105 ml). The suspension was stirred at room temperature while a solution of sodium hydroxide (8.8 g, 0.22 mol) in water (50 ml) was added dropwise over 20 minutes, maintaining the reaction temperature between 20 and 25° C. by water bath cooling. The resultant dark red solution was stirred at room temperature for 15 minutes, diluted with water and acidified to pH1-2 by addition of 2M hydrochloric acid and extracted with ethyl acetate. The organic extract was washed with brine (200 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to give 4-hydroxy-3-nitrophenylacetic acid (19.6 g) as a yellow solid.

Workup

  1. additionwas added dropwise over 20 minutes
  2. temperaturemaintaining the reaction temperature between 20 and 25° C. by water bath
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with brine (200 ml)
  7. dry with materialdried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21d3cf9e814143948d12e097c1689b96
Source dataset
uspto-grants-2003_04
Patent number
US06544989B2

Reaction notes

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