15910-49-3

Basic information

• Product Name: 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-methoxy-
• CAS NO: 15910-49-3
• Molecular Formula: C19H32O2
• Molecular Weight: 292.462
• Mol File: 15910-49-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-methoxy-(15910-49-3)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-one, 2,4,6-tris(1,1-dimethylethyl)-4-methoxy-(15910-49-3)

Safety Data

• Hazardous Substances Data: 15910-49-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 732-26-3 2,4,6-tri-tert-butylphenoxol 
• 1988-75-6 4-bromo-2,4,6-tri-tert-butyl-2,5-cyclohexadiene-1-one 
• 7732-18-5 water 
• 5457-60-3 4-chloro-2,4,6-tri-tert-butylcyclohexa-2,5-dienone 
• 3315-32-0 2,4,6-tri-tert-butylphenoxyl 

Downstream Products

• 489-01-0 2,6-Di-t-butyl-4-methoxyphenol 
• 15910-86-8 3,6-Di-tert.-butyl-guajacol 
• 15910-85-7 3-Methoxy-2,4,6-tri-tert-butyl-cyclohexa-2,5-dien-1-on 
• 110678-05-2 (4S,5S)-2,5-Di-tert-butyl-4-(2,2-dimethyl-propionyl)-4-methoxy-cyclopent-2-enone 
• 150-76-5 4-methoxy-phenol 
• 20031-57-6 2,6-Di-tert-butyl-4-phenylazo-phenol 
• 1975-15-1 2,6,2',6'-tetra-tert-butyl-4,4'-dimethoxy-4,4'-peroxy-bis-cyclohexa-2,5-dienone 
• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 20137-67-1 2,6-di-tert-butyl-4-methoxyphenoxyl radical 
• 2444-28-2 2,6-di-tert-butyl-4-hydroxyphenol 

Relevant articles and documents

Solvolysis of 4-halogeno-4-alkyl-2,6-di-tert-butylcyclohexa-2,5-dienones induced by positive halogen donors as electrophiles

Positive halogen donors such as N-iodosuccinimide (NIS) induce solvolysis of dienones 1, as model 4-halogenocyclohexa-2,5-dienones, in different hydroxylic solvents (ROH), yielding the 4-RO-cyclohexa-2,5-dienones (2). The rate of the solvolysis with NIS is highly dependent on the structure of ROH. The problem of such dependency is overcome by running the reaction in ROH diluted with MeCN, a polar aprotic solvent, in place of pure ROH; the rate of the reaction in the ROH-MeCN solvent mixture is almost independent of the structure (or the polarity) of ROH, and the reaction is completed faster or markedly faster than in neat ROH. The results suggest that the solvolysis rate is controlled by the polarity of the solvent system, although the hydrogen-bond acceptability of MeCN for dilution also accelerates the reaction. A mechanism for the solvolysis is proposed, involving electrophilic attack of a positive halogen donor at the halogen atom of 1, generating the 4-oxocyclohexa-2,5-dienyl cation intermediates (8) via the rate-limiting polar transition states. CSIRO 2013.

Electron transfer between protonated and unprotonated phenoxyl radicals

(Chemical Equation Presented) The reaction of phenoxyl radicals with acids is investigated. 2,4,6-Tri-tert-butylphenoxyl radical (13), a persistent radical, deteriorates in MeOH/PhH in the presence of an acid yielding 4-methoxycyclohexa-2,5-dienone 18a and the parent phenol (14). The reaction is facilitated by a strong acid. Treatment of 2,6-di-tert-butyl-4-methylphenoxyl radical (2), a short-lived radical, generated by dissociation of its dimer, with an acid in MeOH provides 4-methoxycyclohexa-2,5-dienone 4 and the products from disproportionation of 2 including the parent phenol (3). A strong acid in a high concentration favors the formation of 4 while the yield of 3 is always kept high. Oxidation of the parent phenol (33) with PbO2 to generate transient 2,6-di-tert-butylphenoxyl radical (35) in AcOH/H2O containing an added acid provides eventually p-benzoquinone 39 and 4,4′-diphenoquinone 42, the product from dimerization of 35. A strong acid in a high concentration favors the formation of 39. These results suggest that a phenoxyl radical is protonated by an acid and electron transfer takes place from another phenoxyl radical to the protonated phenoxyl radical, thus generating the phenoxyl cation, which can add an oxygen nucleophile, and the phenol (eq 5). The electron transfer is a fast reaction.

Bromide-assisted oxidation of substituted phenols with hydrogen peroxide to the corresponding p-quinol and p-quinol ethers over WO4 2--exchanged layered double hydroxides

A simple and efficient one-pot synthesis of p-quinols and their ethers occurs over tungstate-exchanged layered double hydroxides (WO4 2--LDHs), which catalyze the bromide-assisted oxidation of substituted phenols to the corresponding 4-alkoxy- and 4-hydroxycyclohexa-2,5- dienones in high yields (see scheme).