Nitric Acid → HCID 53739839, compound

HRID 2299239Notes

Reaction equation

HRID 2299239 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 heterogeneous 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-b9accb961db84fa5b5699d4ed72c30de
Source dataset
uspto-grants-2002_12
Patent number
US06495663B1

Reaction notes

Loading…