6891-45-8

Usage

InChI:InChI=1S/C11H16O/c1-3-4-5-10-8-9(2)6-7-11(10)12/h6-8,12H,3-5H2,1-2H3

Upstream product

• 24323-47-5 1-(2-hydroxy-5-methylphenyl)butan-1-one 
• 109-65-9 1-bromo-butane 
• 106-44-5 p-cresol 
• 917-54-4 methyllithium 
• 591-51-5 phenyllithium 
• 106-51-4 p-benzoquinone 
• 109-72-8 n-butyllithium 
• 18062-76-5 4-(3-chloro-2-butenoxy)toluene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 71-36-3 butan-1-ol 
• 114534-30-4 1-Butyl-4-methyl-cyclohexa-2,5-diene-1,4-diol 
• 72653-47-5 α-chlorobutyl phenyl sulfide 

Downstream Products

• 109221-55-8 2-butyl-6-chloromethyl-4-methyl-phenol 
• 115099-05-3 3,3'-dibutyl-5,5'-dimethyl-bibenzyl-2,2'-diol 

Relevant academic research and scientific papers

On the mechanism of the dimethyldioxirane oxidation of σ(H) adducts (Meisenheimer complexes) generated from nitroarenes and carbanions

The mechanism of the novel dimethyldioxirane (DMD) oxidation of σ(H) adducts (Meisenheimer complexes) generated from nitroarenes and carbanions was elucidated. The proposed mechanism, which is akin to that of the oxidative Nef reaction, is supported by the isolation of the cyclohexadienone intermediate and the lack of a primary kinetic isotopic effect. Protic solvents (H2O, MeOH) enhance the reactivity of DMD through intermolecular hydrogen bonding.

Easy synthesis of 2,4-dialkyl substituted phenols and anisoles from p-benzoquinone

The reaction of p-benzoquinone (1) with several organolithium compounds (methyl-, ethyl-, n-butyl, phenyllithium) leads directly, after acid hydrolysis, to the corresponding 2,4-dialkylphenols 4a-d, resulting from a rearrangement/aromatization process of the corresponding intermediate diols 3. The use of two different alkyllithium reagents leads to the mixed products 4e f. Alternatively, the same results are obtained treating the crude isolated diols 3 with a catalytic amount of concentrated sulfuric acid. Applying this last methodology to the diethers 2, 2,4-dialkylanisoles 8 are obtained. A possible mechanism is proposed.

Preparation and Reactions of Dianions from the Cresols

With n-BuLi/KO-t-Bu, protons are removed from the hydroxyl and methyl groups of cresols 5 to give dianions 6 in yields of 85percent (ortho), 95percent (meta), and 42percent (para).These dianions react with alkyl halides, Me3SiCl, Bu3SnCl, CO2, and oxidizing agents at carbon only and with dialkyl sulfates at both carbon and oxygen.Thus phenol derivatives bearing primary alkyl groups can be prepared from the corresponding methylphenols via dianions 6.