56207-20-6

Upstream product

• 4130-42-1 2,6-di-tert-butyl-4-ethylphenol 
• 69901-40-2 1-ethyl-3,5-di-tert-butyl-4-oxo-2,5-cyclohexadienyl 3,5-di-tert-butyl-4-hydroxyperbenzoate 
• 62926-72-1 Ethaneperoxoic acid 3,5-di-tert-butyl-1-ethyl-4-oxo-cyclohexa-2,5-dienyl ester 

Downstream Products

• 4130-42-1 2,6-di-tert-butyl-4-ethylphenol 
• 59313-71-2 3-Ethyl-2,6-di-tert-butyl-p-benzochinon 
• 59313-65-4 3-Ethyl-2,6-di-tert.-butylhydrochinon 

Relevant academic research and scientific papers

CsOH catalyzed aerobic oxidative synthesis of p-quinols from multi-alkyl phenols under mild conditions

p-Quinols are ubiquitous structural motifs of various natural products and pharmaceutical compounds, and versatile building blocks in synthetic chemistry. The reported methods for the synthesis of p-quinol require stoichiometric amounts of oxidants. Molecular oxygen is considered as an ideal oxidant due to its natural, inexpensive, and environmentally friendly characteristics. During the ongoing research of C-H bond hydroxylation, we found that multi-alkyl phenols could react with molecular oxygen under mild conditions. Herein, we describe an efficient oxidative de-aromatization of multi-alkyl phenols to p-quinols. 1 atm of molecular oxygen was used as the oxidant. Many multi-alkyl phenols could react smoothly at room temperature. Isotopic labeling experiment was also performed, and the result proved that the oxygen atom in the produced hydroxyl group is from molecular oxygen.

P-quinols and p-quinol Ethers from 2,4,6-trialkylphenols

The oxidation of 2,4,6-trialkylphenols with lead(IV) oxide and 70% perchloric acid in water-acetone or in alcohols gives p-quinols or p-quinol ethers, respectively. Some nonmetallic oxidants serve the same purpose. Georg Thieme Verlag Stuttgart.

Peroxy Esters. 9. Base- and Radical-Induced Decomposition of 1-Alkyl-3,5-di-tert-butyl-4-oxo-2,5-cyclohexadienyl 3,5-Di-tert-butyl-4-hydroxyperbenzoates

The title peroxy esters 1, when deprotonated with t-BuOK in DMF to the corresponding phenolate anions, decompose even at -78 deg C to give compounds 2-10.These compounds result undoubtedly from homolysis of the peroxy bond in 1, indicating that the generation of a carbanion at the α-position of the acyl group in peroxy esters (via resonance in the present case) induces ready homolysis of the peroxy bond.The oxidation of 1 with one-electron oxidizing agents gives rise to the corresponding phenoxy radicals, which also induce homolysis of the peroxy bond.

Peroxy Esters. 8. Base-Catalyzed Rearrangement of Peroxy Esters: Formation of Alkoxyacetic Acid Derivatives

p-Peroxyquinol esters derived from base-catalyzed oxygenation of 4-alkyl-2,6-tert-butylphenols followed by Schotten-Baumann acylation undergo a novel base-catalyzed rearrangement with t-BuOK in N,N-dimethylformamide to give p-quinoxyacetic acid derivatives in excellent yield.The same base-catalyzed rearrangement was also observed with tert-butyl peroxy esters.The base-catalyzed reaction of peroxy esters depended strongly on the nature of the acyl group in the esters and the base used and is suggested to involve homolysis of the peroxy bond.

MECHANISM OF SELECTIVE p-QUINOL FORMATION IN THE COBALT SCHIFF BASE COMPLEX-CATALYZED OXYGENATION OF 4-ALKYL-2,6-DI-t-BUTYLPHENOLS

The selective formation of p-quinols in the Co(Salpr)-catalyzed oxygenation of 4-alkyl-2,6-di-t-butylphenols in MeOH has been found to involve the rate determining reduction of peroxy-p-quinolato Co(III) complex formed in the initial fast step.An ionic me