Nitric Acid → HCID 14802112, compound

HRID 329714Notes

Reaction equation

HRID 329714 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:3]=1.[N+:19]([O-])([OH:21])=[O:20]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:14]=[C:13]([N+:19]([O-:21])=[O:20])[C:5]([O:6][CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2728538methyl 5-chloro-2-(2-ethoxy-2-oxoethoxy)benzoate

Product 1

HCID 14802112HCID 14802112, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 620 g of ethyl 4-chloro-2-methoxycarbonylphenoxyacetate in 1600 ml of concentrated sulfuric acid is cooled below 0° C, and a mixture of 102 ml of fuming nitric acid (d 1.50) and 102 ml of concentrated sulfuric acid is added dropwise below 5° C. The resultant solution is stirred for 3 hours under ice-cooling and poured into ice-cold water and then extracted with ethyl acetate. The extract is washed with water twice and dried over magnesium sulfate. The solvent is distilled off and the residue is gradually crystallized to give 697 g of ethyl 4-chloro-2-methoxycarbonyl-6-nitrophenoxyacetate, melting at 68°-70° C.

Workup

  1. additionis added dropwise below 5° C
  2. temperaturecooling
  3. additionpoured into ice-cold water
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with water twice
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. customthe residue is gradually crystallized

Sources & evidence

ORD record
ord-1e2bbc488004447785c3731202cc5b44
Source dataset
uspto-grants-1990_01
Patent number
US04892872

Reaction notes

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