Water → 1-Nitrooctadecane

HRID 424294Notes

Reaction equation

HRID 424294 reaction equation
[N:1]([O-:3])=[O:2].[Na+].[CH2:5](N)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O.O.C1(C=C(O)C=C(O)C=1)O.O>CS(C)=O>[N+:1]([CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH3:5])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 15793OctadecylamineHCID 80196Phloroglucinol dihydrateHCID 23668193Sodium Nitrite

Product 1

HCID 115439441-Nitrooctadecane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium nitrite (14.0 g, 0.2 mol) was added to a solution of the dibromide 2 (17.25 g, 0.05 mol) and phloroglucinol dihydrate (16.2 g, 0.1 mol) in DMSO (100 mL) and stirred for 8 h. The reaction mixture was poured into water and extracted with ethyl acetate (3×150 mL). The ethyl acetate solution was washed with water (2×100 mL) sodium chloride solution (2×100 mL), and dried (Na2SO4). Evaporation of ethyl acetate gave an oil, which was purified by silica gel chromatography, (hexane/ethyl acetate, 7/3). Fractions (Rf=0.73 were collected and evaporated to give 3 as a foamy solid. Yield: 2.8 g (22%).

Workup

  1. extractionextracted with ethyl acetate (3×150 mL)
  2. washThe ethyl acetate solution was washed with water (2×100 mL) sodium chloride solution (2×100 mL)
  3. dry with materialdried (Na2SO4)
  4. customEvaporation of ethyl acetate
  5. customgave an oil, which
  6. customwas purified by silica gel chromatography, (hexane/ethyl acetate, 7/3)
  7. customFractions (Rf=0.73 were collected
  8. customevaporated

Sources & evidence

ORD record
ord-53a025db961546e0bf1fafa18cacd352
Source dataset
uspto-grants-2012_01
Patent number
US08105567B2

Reaction notes

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