4-Nitrophenol → p-Nitrophenyl octyl ether

HRID 657462Notes

Reaction equation

HRID 657462 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)([O-:12])=[O:11].[Na]>CS(C)=O>[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])=[CH:15][CH:14]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 81401-BromooctaneHCID 5360545Sodium

Product 1

HCID 142677p-Nitrophenyl octyl etherYield 30%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1-bromooctane (1 g, 5.18 mmole) and 4-nitrophenol, sodium salt (0.92 g, 5.71 mmole) were refluxed in DMSO (30 ml) at 120° C. for 5 hours. The DMSO was distilled off to near dryness. The resulting brown residue was loaded onto a silica column and eluted with 10:1 mixture of petroleum ether and diethylether. The yield was 30%. 1H NMR (CDCl3, peaks at =8.18 (m, 2H), 6.93 (m, 2H), 4.04 (t, 2H), 1.81 (p, 2H), 1.33 (m, 10H), 0.89 (t, 3H)). Elemental analysis calculated for C14H21O3N: C, 66.91; H, 8.42; N, 5.57. Found: C, 66.97; H, 8.34; N, 5.52.

Workup

  1. distillationThe DMSO was distilled off
  2. washeluted with 10:1 mixture of petroleum ether and diethylether

Sources & evidence

ORD record
ord-8ef2b0ea82fd4c9583551324b01cffd6
Source dataset
uspto-grants-2011_12
Patent number
US08076114B2

Reaction notes

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