Nitric Acid → HCID 20279323, compound

HRID 1248279Notes

Reaction equation

HRID 1248279 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([CH3:16])[C:5]([O:6][CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH3:17])[CH:3]=1.BrC1C=C(C)C(O)=C(C)C=1.[N+:28]([O-])([OH:30])=[O:29]>S(=O)(=O)(O)O.O>[Br:1][C:2]1[CH:15]=[C:14]([CH3:16])[C:5]([O:6][CH:7]([CH3:13])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:4]([CH3:17])[C:3]=1[N+:28]([O-:30])=[O:29]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 169194-Bromo-2,6-dimethylphenolHCID 20279300HCID 20279300, compound

Product 1

HCID 20279323HCID 20279323, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

Ethyl 2-(4-bromo-2,6-dimethylphenoxy)propanoate (92.8 g, 307 mmole), prepared by the method of Example 1 from 4-bromo-2,6-dimethylphenol, was dissolved in 320 ml of cold (-10°) concentrated sulfuric acid. While maintaining the temperature below 0°, 22.4 ml of 70% nitric acid was added slowly. After fifteen minutes the reaction mixture was poured onto ice and diluted to 1.0 l with water, then extracted with two portions of diethyl ether. The organic portion was washed repeatedly with aqueous sodium bicarbonate and then with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to dryness. Chromatography on silica gel (ethyl acetate-hexane eluent) afforded the title compound. Structure assignment was supported by nmr and infrared spectra.

Workup

  1. additionwas added slowly
  2. additionAfter fifteen minutes the reaction mixture was poured onto ice
  3. extractionextracted with two portions of diethyl ether
  4. washThe organic portion was washed repeatedly with aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-266e5a939b87469f9819ed8e7a30807b
Source dataset
uspto-grants-1985_06
Patent number
US04523020

Reaction notes

Loading…