13395-07-8

Upstream product

• 2409-55-4 2-tert-Butyl-4-methylphenol 
• 128-37-0 2,6-di-tert-butyl-4-methyl-phenol 
• 78074-81-4 5-t-butyl-7-methyl-1-oxaspiro<2,5>octa-5,7-dien-4-one 
• 25844-12-6 2-hydroxy-5-methyl-3-tert-butylbenzyl alcohol 
• 10396-80-2 2,6-di-tert-butyl-4-hydroxy-4-methylcyclohexa-2,5-dienone 

Downstream Products

• 65678-12-8 2-chloro-4-formyl-6-t-butylphenol 
• 1131688-17-9 C₁₄H₁₉ClO 

Relevant academic research and scientific papers

Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp 2)-H Alkylation with Nitroalkanes

We report studies toward a small-molecule-catalytic approach to access atropisomeric diaryl ethers that proceeds through a C(sp 2)-H alkylation using nitroalkanes as the alkyl source. A quaternary ammonium salt derived from quinine, containing

Highly Selective Aromatic Chlorinations. Part 2. The Chlorination of Substituted Phenols, Anisoles, Anilines, and Related Compounds with N-Chloroamines in Acidic Solution

Phenols, anisoles, anilines, and related compounds are chlorinated in trifluoroacetic acid at room temperature by N-chlorodialkylamines and N-chlorotrialkylammonium salts.With monsubstituted compounds and their 2- and 3-substituted derivatives the reaction occurs efficiently and selectively at the 4-position.The reactivity of these substrates and the selectivity of their chlorinations are determined by electronic rather than steric effects of the substituent.Blocking the reaction with a substituent at the 4-position generally leads to only poor or moderate yields of the 2-chlorinated product.Evidence for radical and cation radical intermediates has been obtained in the reactions of some of the 4-substituted reactants and the mechanism of chlorination is discussed in the light of these findings.The reactions of selected substrates have been scaled up to give laboratory syntheses.

Reactions of 1-Oxaspiroocta-5,7-dien-4-ones with Nucleophiles

The 1-oxaspiroocta-5,7-dien-4-ones (6-spiroepoxy-2,4-cyclohexadienones) (7) on reaction with a number of carbon, nitrogen, oxygen and halogen nucleophiles produced a variety of interesting substitution and rearrangement products (8)-(19) in moderate yields.The products derived almost exclusively from initial attack of the nucleophile with either the secondary or quaternary carbon of the epoxy ring and these various modes of reaction of the spirocyclic system are discussed.The formation of ortho-substituted phenols from the 1-oxaspiroocta-5,7-dien-4-ones suggests that the latter structures may be regarded as polarity-reversed masked phenols.Tropolones, products of a possible ring-expansion reaction, were not observed in any of the reactions investigated.

OXIDATIVE COUPLING REACTION OF 2-HALOPHENOLS WITH K3Fe(CN)6 IN BENZENE SOLUTION

The oxidative coupling of twelve 2-halophenols (1a-1l) was carried out with K3Fe(CN)6 in benzene solution to obtain the corresponding dibenzofuran derivatives.However, only a small amount of the desired dibenzofurans such as 2,6-di-tert-butyl-8-methoxybenzofuran-1,4-quinone (9) and 4,8-di-tert-butyl-2,6-di-isopropyl-1-hydroxydibenzofuran (11) were obtained from 2-bromo-6-tert-butyl-4-methoxy- (1d) and 2-bromo-4-tert-butyl-6-isopropylphenol (1g), respectively.In the other cases, alternative type of products or tarry materials were formed.