Butyl 2-nitrophenyl ether

Cognate preparations. Butyl 2-nitrophenyl ether (o-Butoxynitrobenzene). Place a mixture of 28 g (0.2 mol) of o-nitrophenol (Expt 6.102), 28 g (0.2 mol) of anhydrous potassium carbonate, 30g (23.5 ml, 0.22 mol) of butyl bromide and 200 ml of dry acetone in a 1-litre round-bottomed flask fitted with an efficient reflux condenser, and reflux on a steam bath for 48 hours. Distil off the acetone, add 200 ml of water and extract the product with two 100 ml portions of benzene (CAUTION). Wash the combined benzene extracts with three 90 ml portions of 10 per cent sodium hydroxide solution, remove the benzene by distillation at atmospheric pressure and distil the residue under reduced pressure. Collect the o-butoxynitrobenzene at 171-172°C/19mmHg (or at 127-129 °C/2mmHg) the yield is 30 g (77%). 

The third step was the conversation of l-(2-aminoethyl)-3-(2,6-dichloro-4-nitrophenyl)-thiourea ethylenediamine solvate to 2-[(2,6-dicloro-4-nitrophenyl)imino]imidazoline ethylenediamine solvate. (500 g, 1.35 mol) of above prepared thiourea solvate was suspended with toluene (4 L) and was heated at reflux for 15 hours. The mixture was cooled to 23°C and 1 M aqueous hydrochloric acid (4 L) was added. After stirring for 10 min the biphasic mixture was filtered to remove a sticky insoluble material. The aqueous phase was neutralized to pH=7.0 using 50% NaOH. After stirring for 1 hour the yellow solid was collected by filtration, washed with water (4 L) and t-butyl methyl ether (2 L) and dried in air to constant weight of 195 g (52%), m.p. 289-292°C. 

The fourth step was the conversation of 2-[2,6-dichloro-4-nitrophenyl) imino]imidazoline (150 g, 0.55 mol) in methanol (1,5 L) to 2-[(2,6-dichloro-4-aminophenyl)imino]imidazoline by hydrogen with 30 g Raney nickel catalyst at 23°C for 22 hours. After removing the catalyst hydrogen chloride gas was bubbled into solution until pH of the reaction mixture was 1.0. The solvent was rotary removed in vacuum and the residual solid was slurried with 2-propanol (1 L). The solvent was again removed by rotary evaporation, the cream solid was triturated with 2-propanol (600 ml). After aging for 1 hour, the solid was collected by filtration, washed with 2-propanol and t-butyl methyl ether, and dried for 15 hours at 6°C and t-butyl methyl ether, and dried for 15 hours at 60°C and 20 mm Hg. Yield of dihydrochloride 167 g... 

C10H14NO4P diethyiphosphinic acid p-nitrophenyl ester 7531-39-7 399.15 34.285 1.2 20038 C10H14O butyl phenyl ether 1126-79-0 483.15 42.268 1,2... 

Common names butyl p-nitrophenyl ether CA number [7244-78-2]... 

Butyl p-Nitrophenyl Ether Preparation Using a Monomode Microwave Apparatus... 

Weigh the pure butyl p-nitrophenyl ether and calculate the percent yield. Determine the melting point and compare the experimental values with those in the literature. 

Obtain an IR spectrum of the compound and compare it to that shown in Figure 6.42 for 4-butoxy nitrobenzene (butyl p-nitrophenyl ether). 

Nuclear Magnetic Resonance Analysis. If facilities permit, you can obtain both and NMR spectra of your butyl p-nitrophenyl ether in CDCl... 

Figure 6.42 HATR-IR spectrum butyl p-nitrophenyl ether.

Problem 14.55 Prepare the following ethers starting with benzene, toluene, phenol (C H OH), cyclohexanol, any aliphatic compound of three C s or less and any solvent or inorganic reagent a) dibenzyl ether, b) di-/i-butyl ether, (c) ethyl isopropyl ether, d) cyclohexyl methyl ether, (e) p-nitrophenyl ethyl ether, (/) divinyl ether (g) diphenyl ether. <... 

Organic azides combine with open-chain and cyclic eno) ethers to give A -triazolines in high yield. The addition is stereospecific cis and the orientation process is determined by electronic effects.145-160 The triazolines are unstable above 100° and can decompose in mainly two ways. 44 Triazolines from the open-chain enol ethers, vinyl butyl ether, /S-ethoxypropene, and a- and /3-methoxystyrene, eliminate alcohol thermally and are converted into 1,2,3-triazoles. For example, the triazoline 67 from /J-ethoxypropene 66 and p-nitrophenyl azide decomposes quantitatively at 150° into l-(p-nitrophenyl)-5-methyl-1,2,3-triazole (68). 

Synthesis of[ 1-11C]-labelled ethyl, propyl, butyl and isobutyl iodides, and N-[1-11 C-ethyl]lidocaine, 178, N-[1-11C-butyl]bupivacaine, 179, and 3-nitrophenyl [1-11C]propyl ether, 180... 

---