4-Nitro-3-hexanol

The reduction of nitrobenzene to aniline is a major industrial process at the heart of the production of polyurethanes, and it is also often used as a marker reaction to compare activities of catalysts [1,2], It can be performed over a variety of catalysts and in a variety of solvents. As well as its main use in polymethanes, aniline is used in a wide range of industries such as dyes, agrochemicals, by further reaction and functionalisation. Reductive alkylation is one such way of functionalising aromatic amines [3, 4], The reaction usually takes place between an amine and a ketone, aldehyde or alcohol. However it is possible to reductively alkylate direct from the nitro precursor to the amine and in this way remove a processing step. In this study we examined the reductive alkylation of nitrobenzene and aniline by 1-hexanol. 

Ref 1), RI at 25° 1.4462. Prepd by treating Et2NH aq with aq HCHO (37%) then with CsHi iN02 to give 2-nitrohexyldiethylamine whose HC1 salt is pyrolyzed to yield the desired nitroalkene (Ref 2) also by distilling under reduced pressure 2-nitro-l-hexanol phthallic-anhydride (Ref 3)... 

Meng and Sode [35, 36] also reported the preparation of imprinted polymers to be used as reaction vessels for the transesterification of p-nitro-phenol acetate (23) and hexanol. The MIP showed eightfold increased activity when compared to the NIP. 

Harnstoff l-Butyl-3-ethoxycarbonyl-E4,1035 [OC(OR)2 + Harnstoff] Hexan 2-Acetamino-l-nitro- E16d, 162 (En + NO + R-CN) 3-Hexanol 2,5-Bis-[hydroximino]-... 

Dinitrohexane, N02CH2CH(N02)C4H9 liq. Prepd by reacting 1-hexane with an equilibrium mixt of N02 N204 to give 1,2-dinitrohexane l-nitro-2-hexanol nitrite... 

The reaction is most useful for the preparation of olefinic, halo, and nitro alcohols from the corresponding substituted aldehydes and ketones. These substituents ate very often affected by other reduction procedures. Excellent directions are found in the preparations of crotyl alcohol (60%), l-bromo-5-hexanol (64%), l-chloco-4-pentanol (76%), /S,/S,/S-trichloroethyl alcohol (84%), methyl-p-chlorophenylcarbinol (81%), and o-nitrobenzyl alcohol (90%). The reaction has also been used in the preparation of certain tetralols and decalols as well as 9-fluo-renylcarbinol (50%). The thiophene and furan nuclei are not reduced. 

B. 4-Acetoxy-3-nitrohexane (2).3 To the above flask, containing 3-nitro-4-hexanol (330 g, 2.24 mol), is added a magnetic stirring egg and 1 mL of coned sulfuric add. The contents of the flask are stirred In an ice bath and acetic anhydride (240 g,... 

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