Butyltoluene

Trinitro-3-tert-butyltoluene, m.p. 97°C, yellow crystals. Used in perfumery and known as musk hour. 

The reaction of N bromosuccimmide with the following com pounds has been reported in the chemical literature Each compound yields a single product in 95% yield Identify the product formed from each starting material (a) p-tert Butyltoluene (b) 4 Methyl 3 nitroanisole... 

When two positions are comparably activated by alkyl groups substitution usually occurs at the less hindered site Nitration of p tert butyltoluene takes place at positions ortho to the methyl group m preference to those ortho to the larger tert butyl group This IS an example of a stenc effect... 

Miscellaneous Derivatives. Other derivatives of toluene, none of which is estimated to consume more than ca 3000 t (10 gal) of toluene aimuaHy, are mono- and dinitrotoluene hydrogenated to amines ben2otrich1 oride and chlorotoluene, both used as dye intermediates / 7-butylben2oic acid from / 7-butyltoluene, used as a resin modifier dodecyltoluene converted to a ben2yl quaternary ammonium salt for use as a germicide and biphenyl, obtained as by-product during demethylation, used in specialty chemicals. Toluene is also used as a denaturant in specially denatured alcohol (SDA) formulas 2-B and 12-A. 

Dichlorotoluene (l,3-dichloro-2-methylben2ene) is prepared from the Sandmeyer reaction on 2-arnino-6-chlorotoluene. Other methods include ring chlorination of -toluenesulfonyl chloride followed by desulfonylation (81), and chlorination and dealkylation of 4-/ f2 -butyltoluene (82) or... 

The nitration of 2,4,6-tri-t-butyltoluene gives rise to three products. The distribution is changed when the 3- and 5-positions are deuterated ... 

Butyl ether Butyl carbitol /i-Butyl glycidyl ether Butyl mercaptan p-tert-Butyltoluene Carbon disulphide Carbon dioxide Carbon monoxide Carbon tetrachloride Carbonyl sulphide Carbary ... 

Butyl cellosolve (2-butoxy ethanol) n-Butyl glycidyl ether n-Butyl mercaptan n-Butylamine p-tert-Butyltoluene... 

Butyl cellosolve, see 2-Butoxyethanol tert-Butyl chromate (as CrOj) n-Butyl glycidyl ether n-Butyl lactate Butyl mercaptan p-tert-Butyltoluene Cadmium, dust and salts (as Cd) Cadmium, fume (as Cd)... 

Oxidation of/)-ter/-butyltoluene Br-promoted Co p-tert-Butyl- Fine chemicals,... 

Ring-substituted benzyl alcohols sometimes undergo such reduction more effectively than unsubstituted alcohols. For example, treatment of a dichloromethane solution of 2,4,6-trimethylbenzyl alcohol with trifluoroacetic acid and triphenylsilane produces a 41% isolated (89% by GLC) yield of isodurene.26 Treatment of 2-me(hyl-4,6-di-/m-buty I benzyl alcohol with a three-fold excess of triethylsilane and trifluoroacetic acid in dichloromethane at room temperature gives an 85% yield of 2-mclhyl-4,6-di-/m-butyltoluene together with 15% of 3,5-di-ferf-butyltoluene. The latter is presumably formed by loss of protonated formaldehyde from the Cl ring-protonated substrate.128 Similar treatment of 2,4,6-tri-ferf-butylbenzyl alcohol produces a 90% yield of 2,4,6-tri-tert-butyltoluene within one hour (Eq. 21).128... 

Dichloromethane solutions of some sterically congested benzyl chlorides and triethylsilane need only the addition of excess trifluoroacetic acid to promote rapid conversion of the chlorides to the related hydrocarbons.128 Thus 2,4,6-trimethylbenzyl chloride produces a 79% yield of isodurene at room temperature after 2.5 hours, 2-methyl-4,6-di-/m-bu(ylbenzyl chloride gives 50% 1, 2-di-methyl-4,6-di-tm-butylbenzene after 40 minutes at reflux, and 2,4,6-tm-butyl-benzyl chloride gives a 100% yield of 2,4,6-tri-rm-butyltoluene within 17 minutes at reflux (Eq. 54). The unsubstituted parent benzyl chloride remains unreacted under these conditions even after 30 days.128... 

Scheme 60 Selective side-chain oxidation of 4 — t-butyltoluene with cerium (IV) as mediator.

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