Nitric Acid → 2-(2-Carboxy-4-chloro-6-nitrophenoxy)propionic acid

HRID 329709Notes

Reaction equation

HRID 329709 reaction equation
[C:1]([C:4]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:5]=1[O:6][CH:7]([CH3:11])[C:8]([OH:10])=[O:9])([OH:3])=[O:2].[N+:17]([O-])([OH:19])=[O:18]>S(=O)(=O)(O)O>[C:1]([C:4]1[CH:15]=[C:14]([Cl:16])[CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:5]=1[O:6][CH:7]([CH3:11])[C:8]([OH:10])=[O:9])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 147715362-(2-Carboxy-4-chlorophenoxy) propionic acid

Product 1

HCID 145172302-(2-Carboxy-4-chloro-6-nitrophenoxy)propionic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 220 g of 2-(2-carboxy-4-chlorophenoxy) propionic acid in 550 ml of concentrated sulfuric acid is added dropwise a mixed liquid of 44 ml of fuming nitric acid and concentrated sulfuric acid under stirring with keeping at a temperature below 10° C. After the addition, the reaction mixture is stirred below 10° C. for 3 hours and poured into 10 1 of ice-cold water. The precipitated crystals are collected by filtration, washed with 2 1 of water four times and them dried to give 190 g of 2-(2-carboxy-4-chloro-6-nitrophenoxy)propionic acid, melting at 190° C.

Workup

  1. customwith keeping at a temperature below 10° C
  2. additionAfter the addition
  3. stirringthe reaction mixture is stirred below 10° C. for 3 hours
  4. additionpoured into 10 1 of ice-cold water
  5. filtrationThe precipitated crystals are collected by filtration
  6. washwashed with 2 1 of water four times and them
  7. customdried

Sources & evidence

ORD record
ord-ac609c9673104f348d7d9238f75a69d4
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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