Nitric Acid → 1-(4-Cyclohexyl-3-nitrophenyl)ethanone

HRID 1777329Notes

Reaction equation

HRID 1777329 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]1([C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>S(=O)(=O)(O)O>[CH:5]1([C:11]2[CH:12]=[CH:13][C:14]([C:17](=[O:19])[CH3:18])=[CH:15][C:16]=2[N+:1]([O-:4])=[O:2])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 877151-(4-Cyclohexylphenyl)ethan-1-one

Product 1

HCID 219966001-(4-Cyclohexyl-3-nitrophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A mixture of concentrated sulfuric acid & nitric acid (68-72%) (1.7:6, 15 mL) is added drop wise to a cold solution of 1-(4-cyclohexylphenyl)ethanone (6 g, 0.03 mol) in concentrated sulfuric acid (15 mL) at 0-5° C. Reaction mixture is allowed to stir at this temperature for 30 minutes & is then poured into crushed ice. It is then extracted with ethyl acetate (3×40 mL). Combined organic layer is dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography (silica gel, 230-400 mesh, ethyl acetate:n-hexane 1:9) to yield 1-(4-cyclohexyl-3-nitrophenyl)ethanone.

Workup

  1. customReaction mixture
  2. additionis then poured
  3. custominto crushed ice
  4. extractionIt is then extracted with ethyl acetate (3×40 mL)
  5. dry with materialCombined organic layer is dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography (silica gel, 230-400 mesh, ethyl acetate:n-hexane 1:9)

Sources & evidence

ORD record
ord-e678a84ecf354800b91ac49a274e33c1
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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