Nitric Acid → 2-Nitro-6-n-propylphenol

HRID 1723003Notes

Reaction equation

HRID 1723003 reaction equation
O.[CH2:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])[CH2:3][CH3:4].[N+:12]([O-])([OH:14])=[O:13]>CCOCC>[CH2:2]([C:5]1[C:6]([OH:11])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:9][CH:10]=1)[CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 125702-Propylphenol

Product 1

HCID 150363142-Nitro-6-n-propylphenol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 100 ml of water, 100 ml of ether and 10.0 g of 2-n-propylphenol was added dropwise 11.0 ml of 61% nitric acid and the reaction was carried out with stirring at room temperature for 12 days. The reaction mixture was extracted with 200 ml of ethyl acetate and dried with anhydrous sodium sulfate. The drying agent was filtered off and the solvent was distilled away under reduced pressure. The residue was purified by subjecting to silica-gel column-chromatography [eluent: chloroform-n-hexane (1 : 1)]to give 3.76 g of 6-n-propyl-2-nitrophenol.

Workup

  1. extractionThe reaction mixture was extracted with 200 ml of ethyl acetate
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationThe drying agent was filtered off
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-43718f98701a4104b727103d53041b5a
Source dataset
uspto-grants-1989_08
Patent number
US04859661

Reaction notes

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