4-tert-Butyl-2,6-dimethylphenol

PEROXIDES AND PEROXIDE COMPOUNDS - ORGANIC PEROXIDES] (Vol 18) 2-tert-Butyl-4,6-dimethylphenol [1879-09-0]... 

McCracken, P. G. Bolton, J. L. Thatcher, G. R. J. Covalent modification of proteins and peptides by the quinone methide from 2-tert-butyl-4,6-dimethylphenol selectivity and reactivity with respect to competitive hydration. J. Org. Chem. 1997, 62, 1820-1825. 

The oxidative polymerization reaction is rapid at room temperature. Oxidation of 2.6-dimethylphenol readily gives high polymer with only a minor amount of the diphenoquinone (VIII R=R1=CH3). This polymer is now being produced commercially. In general when the substituents are small (Table 4) the polymer is formed preferentially (35). If one of the substituents is as large as tert-butyl or both as large as isopropyl then the diphenoquinone is preferentially formed. 

Phenols/cresols Phenol, 2,5-dimethylphenol, 3,5-dimethylphenol, 2,6-di-tert-butyl-4-methylphenol, o,m,p-cresol, p-tetramethylbutylphenol, nonylphenols, 2,6-di-tert-butyl-4-methoxymethylphenol, 2,6-di-tert-butyl-4-methylphenol, 4,4 -butyliden-bis-(6-tert-butyl) -m-cresol, C-8-alkylphenols, C-9-alkylphenols... 

Pd-catalyzed CO- bond forming reactions were performed by Buchwald [8] et al. with 2-dimethylamino-2 -di-(tert.-butyl)-biphenyl as ligand. 3,4-Dimethylphenol can be arylated smoothly with 2-chloro-4-methyl-toluene in the presence of sodium hydride [eq. (f)]. 

Polycondensates were prepared from pyrocatechol, o-cresol, p-cresol, mixtures of the latter with 2,4-dimethylphenol,2-tert-butyl-4-methylphenol, di-scc-butyl-phenol or other monoalkylphenols and their mixtures with dialkylphenols or alkoxyphenols. 

Cl2H17Br02 1-bromO 3-adamantyl hydroxymethyl ketone 73599-91-4 526.15 46.402 1,2 24433 C12H180 2-tert-butyl-4,5-dimethylphenol 1445-23-4 531.65 46.933 1,2... 

C11H25N diethylheptyl amine 26981-81-7 215.00 27.267 2 24434 C12H180 2-tert-butyl-4,6-dimethylphenol 1879-09-0 295.45 24.372 2... 

C11H25N 4-ethyl-1 -methyl octyfamine 10024-78-9 288.26 35.332 2 24436 C12H180 4-tert-butyl-2,5-dimethylphenol 17696-37-6 344.35 24.372 2... 

Many phenols are oxidized efficiently to quinones by acyl tert-butyl nitroxides in organic solvents. 2,6-Dimethylphenol (206) was oxidized with benzoyl tert-butyl nitroxide in CH2CI2 at room temperature to afford 2,6-dimethyl-p-benzoquinone (223) in 86% yield. Oxidation of 2,4,6-trimethylphenol (221) was also effected with the same reagent in ether to afford the A-fert-butylbenzohydroxamic acid 568 in 98% yield (Scheme 105) . 

Dimethylphenol (206) was treated with NaBiOs in benzene to afford polyphenylene oxide (659) and 3,3, 5,5 -tetramethyldiphenoquinone (207) in 74 and 12% yields, respectively . This result is similar to that of Mn02 oxidation (see Scheme 126). In contrast, the use of AcOH instead of benzene as a solvent provided the corresponding quinol acetate 864 and 207 in 38 and 15% yields, respectively (Scheme 174) °. Oxidation of 2,4,6-tri(tert-butyl)phenol (73) with NaBiOs in AcOH afforded the p-quinol acetate (865) as a major product (62%) and the o-quinol acetate (866) as a minor product (22%). In contrast, Pb(OAc)4 oxidation of 73 in AcOH provided 866 as a main product (60%) (see Scheme 170). Oxidation of alkoxyphenols and other phenols has also been studied . ... 

To tert-butyl bromide was added 2,6-dimethylphenol in carbon tetrachloride containing silica gel and sodium carbonate and the mixture refluxed (24 h) to give 2,6-dimethyl-4-tert-butylphenol. 

The methylphenols (cresols and the dimethylphenols (xylenols) also respond to alkylation although this procedure is practically exclusively confined to the tert-butyl series. For example, the majority of compounds produced are hindered or crypto phenols the chemistry of which has been discussed in an earlier chapter. For these alkylations a small proportion of sulphuric acid is employed at moderate temperatures. When more valuable alkenes are involved and the objective is the yield of product, boron trifluoride is favoured as a catalyst. 

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