Nitric Acid → 2-Nitro-4-propylphenol

HRID 1913680Notes

Reaction equation

HRID 1913680 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)C>[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 125804-Propylphenol

Product 1

HCID 2405532-Nitro-4-propylphenolYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a mixture of 5.0 g of 4-propylphenol and 35 ml of acetic acid, a mixture of 3.80 g of 61% nitric acid and 10 ml of acetic acid was added dropwise with the temperature kept at 10-15° C., which was stirred for four hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure to give 6.65 g of 4-propyl-2-nitrophenol.

Workup

  1. additionwas added dropwise with the temperature
  2. customkept at 10-15° C.
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-736cccfc515f4d6abcfa6cf0df5c3ac2
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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