Nitric Acid → 4-Dodecyl-2-nitrophenol

HRID 249232Notes

Reaction equation

HRID 249232 reaction equation
[CH2:1]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N+:20]([O-])([OH:22])=[O:21]>C(O)(=O)C>[CH2:1]([C:13]1[CH:14]=[CH:15][C:16]([OH:19])=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 660304-Dodecylphenol2×

Product 1

HCID 113812644-Dodecyl-2-nitrophenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7.5 g of the 4-dodecylphenol obtained in (1) above was dissolved in 25 ml of acetic acid and 12.6 ml of 30% aqueous nitric acid solution was dropwise added slowly to the resulting solution, and then the resulting mixture was subjected to reaction at about 10° C. for one hour. The reaction mixture was added to 35 g of ice water and the extraction with 35 ml of diethyl ether was conducted three times. The diethyl ether layer thus obtained was washed with 35 ml of 5% aqueous NaHCO3 solution, and then dried with MgSO4. Subsequently, the solvent was distilled off to obtain 5.93 g of 4-dodecyl-2-nitrophenol.

Workup

  1. customthe resulting mixture was subjected to reaction at about 10° C. for one hour
  2. extractionthe extraction with 35 ml of diethyl ether
  3. customThe diethyl ether layer thus obtained
  4. washwas washed with 35 ml of 5% aqueous NaHCO3 solution
  5. dry with materialdried with MgSO4
  6. distillationSubsequently, the solvent was distilled off

Sources & evidence

ORD record
ord-7faf479a0b564d2e9b1ea355922fee25
Source dataset
uspto-grants-1993_05
Patent number
US05213888

Reaction notes

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