2-Ethylphenol → 2-Ethyl-6-nitrophenol

HRID 400600

Reaction equation

HRID 400600 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2].F[B-](F)(F)F.[O:15]=[N+:16]=[O:17]>C(#N)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:16]([O-:17])=[O:15])[C:4]=1[OH:9])[CH3:2]

Participants

4

Reactant 2

HCID 69972-EthylphenolHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 150363132-Ethyl-6-nitrophenolYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-ethylphenol (2.44 g, 20 mmol) in 80 mL of anhydrous acetonitrile was treated with nitronium tetrafluoroborate (2.93 g, 22 mmols) in portions over a period of 5 minutes at −30° C. to −40° C. After 20 minutes, the mixture was quenched with ice, treated with cold water and extracted with three 100 mL portions of dichloromethane. The combined organic layers were washed with two 30 mL portions of water, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (20% ethyl acetate in hexanes) gave 2.0 g of 2-ethyl-6-nitrophenol as a yellow oil (60% yield).

Workup

  1. customthe mixture was quenched with ice
  2. additiontreated with cold water
  3. extractionextracted with three 100 mL portions of dichloromethane
  4. washThe combined organic layers were washed with two 30 mL portions of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ba1b52adac64ee2b33689d216471ae9
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Linked notes

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