Water → 1-Nitrotridecane

HRID 1938732Notes

Reaction equation

HRID 1938732 reaction equation
[N:1]([O-:3])=[O:2].[Na+].Br[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].O>CN(C)C=O>[N+:1]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH3:6])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 130001-BromotridecaneHCID 23668193Sodium Nitrite

Product 1

HCID 108233151-Nitrotridecane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred, room temperature suspension of sodium nitrite (227 g, 3.29 mol) in dimethylformamide (3.8 L) was added 1-bromotridecane (514.51 g, 1.95435 mol), and the mixture was stirred for 6 hours. The mixture was poured into cold water (8 L) and extracted with petroleum ether (2×2 L). The organic layer was washed with water (2 n), saturated sodium chloride, dried (MgSO4), and rotoevaporated to a yellow oil. The oil was distilled in vacuo to give another oil; yield 171.9 g, bp 101°-120° C. (0.2 mm Hg). The oil was chromatographed on silica gel (3.0 kg, 230-400 mesh) using ether/ethyl acetate (100:1, 4×2 L; 80:1, 4×2 L; 50:1, 7×2 L) to give a clear colorless oil; yield 109.8 g (24.5%).

Workup

  1. extractionextracted with petroleum ether (2×2 L)
  2. washThe organic layer was washed with water (2 n), saturated sodium chloride
  3. dry with materialdried (MgSO4)
  4. distillationThe oil was distilled in vacuo
  5. customto give another oil
  6. customThe oil was chromatographed on silica gel (3.0 kg, 230-400 mesh)
  7. customto give a clear colorless oil

Sources & evidence

ORD record
ord-eb72100b763847e18641563f1a9c84e2
Source dataset
uspto-grants-1997_12
Patent number
US05693657

Reaction notes

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