Nitric Acid → HCID 53739839, compound

HRID 381640Notes

Reaction equation

HRID 381640 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[N+:12]([O-])([OH:14])=[O:13]>O>[OH:1][C:2]1[CH:7]=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 11970(2-Hydroxyphenyl)acetic acid

Product 1

HCID 53739839HCID 53739839, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of o-hydroxy phenylacetic acid (15.0 g, 0.099 mol) in H2O (39 mL) at 0° C. was added a solution of nitric acid (12 mL of 65% in 8 mL H2O) slowly via pipette. The solution was stirred for an additional 1.5 h at 0° C. The mixture was then warmed to ambient temperature and allowed to stir for an additional 0.5 h. The heterogenous solution was poured over ice (10 g) and filtered to remove the insoluble ortho-nitro isomer. The reddish solution was concentrated under reduced pressure, and the thick residue was redissolved in 6N HCl and filtered through celite. The solvent was again removed under reduced pressure to provide the desired 2-hydroxy-4-nitro-phenylacetic acid as a light, brownish-red solid (40% yield). The product (IV-a) was used in the next step without further purification.

Workup

  1. temperatureThe mixture was then warmed to ambient temperature
  2. stirringto stir for an additional 0.5 h
  3. filtrationfiltered
  4. customto remove the insoluble ortho-nitro isomer
  5. concentrationThe reddish solution was concentrated under reduced pressure
  6. dissolutionthe thick residue was redissolved in 6N HCl
  7. filtrationfiltered through celite
  8. customThe solvent was again removed under reduced pressure

Sources & evidence

ORD record
ord-62e4a574df5d4cda87ed295cd9b9e8fd
Source dataset
uspto-grants-2001_10
Patent number
US06306993B1

Reaction notes

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