Hydrochloric Acid → 4-Chloro-2-nitrobenzeneacetic acid

HRID 971428Notes

Reaction equation

HRID 971428 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[CH2:11][C:12](=[O:16])C(O)=O)([O-:3])=[O:2].[OH-:17].[Na+].OO.Cl>O>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([CH2:11][C:12]([OH:16])=[O:17])=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide2×HCID 14798Sodium Hydroxide2×HCID 21962448HCID 21962448, compound

Product 1

HCID 2715524-Chloro-2-nitrobenzeneacetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The filtrate of Step A, above, is adjusted to pH 8-9 with 2 N sodium hydroxide and is heated at 35°-40° C. while adding a 3-6% aqueous hydrogen peroxide solution until samples no longer turn dark on treatment with 2 N sodium hydroxide. The tan precipitate is suspended in 1500 ml. of water, adjusted to pH 8-9 and similarly treated with aqueous hydrogen peroxide. The combined reaction mixtures are then acidified with concentrated hydrochloride acid to obtain a precipitate which are recovered by filtration, washed 3 times with water and dried in vacuo. The crude product (mp 145°-150° C.) is recrystallized from ether to obtain 4-chloro-2-nitro-phenylacetic acid, m.p. 156°-159° C.

Workup

  1. temperatureis heated at 35°-40° C.
  2. customThe combined reaction mixtures
  3. customto obtain a precipitate which
  4. filtrationare recovered by filtration
  5. washwashed 3 times with water
  6. customdried in vacuo
  7. customThe crude product (mp 145°-150° C.) is recrystallized from ether

Sources & evidence

ORD record
ord-d8dc923cb1d44e77ac8259b0c4f1ac39
Source dataset
uspto-grants-1979_07
Patent number
US04160032

Reaction notes

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