2.4.6- Trimethylbenzyl alcohol

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... 

Reduction of 2-furoyl chloride [225] at mercury in MeCN containing TEAP affords a variety of products, the most prominent of which is 1,2-di(2-furyl)ethene-l,2-diol di(2-furoate), along with small quantities of 2-furaldehyde, furil, furoin, hydro-furoin, l,2-di(2-furyl)-2-hydroxy-3-cyanopropanone, and 3-(2-furyl)acrylonitrile. Electrolysis of 2,4,6-trimethylbenzoyl chloride [226] at carbon and mercury in MeCN containing TEAP gives mainly 2,4,6-trimethylbenzaldehyde and 3-(2,4,6-trimethylphen-yl)acrylonitrile however, traces of 2,4,6-trimethylbenzene, 2,4,6-trimethylbenzyl alcohol, 3-(2,4,6-trimethylphenyl)glutaronitrile, and 3-(2,4,6-trimethylphenyl)propionitrile are formed. 

The mechanism of the condensation reaction of pseudocumene and formaldehyde showed that trimethylbenzyl alcohols were formed as intermediates. However, these alcohols were not detected in the reaction products because they are more reactive than formaldehyde and condense immediately with pseudocumene to produce the corresponding HexMeDPM (39). 

The alcohol thus obtained can be converted into its chloride and subjected to similar reaction. By three successive such rearrangements, Reichstein and his co-workers108 obtained 2,3,4-trimethylbenzyl alcohol, but the yields in the later stages were unsatisfactory. 

Synonyms Benzenemethanol, a,a,4-trimethyl- 8-p-Cymenol p-Cymen-8-ol Dimethyl p-tolyl carbinol 8-Hydroxy-p-cymene a-Hydroxy-p-cymene p-(Hydroxyisopropyl) toluene 1-Methyl-4-(a-hydroxyisopropyl) benzene 1 -Methyl-4-(1 -hydroxy-1 -methylethyl) benzene 2-(4-Methylphenyl)-2-propanol p-Tolyl dimethyl carbinol 2-(p-Tolyl)-2-propanol a,a,4-Tri methyl benzenemethanol a,a,4-Trimethylbenzyl alcohol p,a,a-Tri methyl benzyl alcohol Empirical C10H14O... 

Tricycio [5.2.1.decane-8-one Trimethylbenzyl alcohol (1 S)-(-)-Verbenone C10H14O2 t-Butylcatechol t-Butyl hydroquinone Camphorquinone Dihydroeugenol Ethyl 2-methoxybenzyl ether Menthalactone Pentyl 2-furyl ketone Phenylacetaldehyde dimethyl acetal C10H14O3 Amyl 2-furoate... 

Primary benzylic cations (monoarylmethyl cations) are not sufficiently stable with respect to equilibration with the parent alcohol to have their pA R+ values determined. The 2,4,6-trimethylbenzyl cation is a rather stable example of this type of carbonium ion, and has a pJ R+ of -17.4, corresponding to equal concentrations of carbonium ion and alcohol in 93% sulfuric acid. 

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