131236-62-9

Upstream product

• 75-91-2 tert.-butylhydroperoxide 
• 131249-98-4 3-Methyl-cyclohexa-1,4-diene-1,3-dicarboxylic acid dimethyl ester 

Downstream Products

• 22481-06-7 dimethyl 3-hydroxy-6-methylbenzene-1,2-dicarboxylate 
• 131236-63-0 dimethyl 4-hydroxy-2-methylbenzene-1,3-dicarboxylate 

Relevant academic research and scientific papers

Allylic functionalization of 2,5- and 2,4-cyclo-hexadiene-1,3- dicarboxylates

A series of 2,4- and 2,5-cyclohexadiene-1,3-dicarboxylates were functionalized at the allylic position via oxidation (SeO2, PDC/t-BuOOH) and halogenation (NBS). The regiochemical outcome for different substrates and reactions was studied mid the importance of factors such as reaction mechanism, steric hindrance and reaction intermediates stability wag discussed.

Photochemical and Acid-Catalyzed Dienone-Phenol Rearrangements. The Effect of Substitutents on the Regioselectivity of 1,4-Sigmatropic Rearrangements of the Type A Intermediate

Birch reduction of isophthalic acid and 3-cyanobenzoic acid followed by (1) methylation of the resulting enolate with methyl iodide and (2) esterification with diazomethane proved 2-carbomethoxy- and 2-cyano-6-methyl-6-carbomethoxy-1,4-cyclohexadienes 9 and 25.Type A photorearrangement of a series of 2-carbomethoxy-, 2-cyano-, 2-methoxy-, and 2-methyl-4-carbomethoxy-4-methyl-2,5-cyclohexadien-1-ones 11, 26, 45a, and 45b gave 4-carbomethoxy-3-methyl-2-substituted-phenols 12, 28, 46, and 31.It has been demonstrated that the regioselectivity of type A photorearrangement of C(2) substituted 2,5-cyclohexadien-1-ones is governed by electronic rather than steric effects to give the intermediate C(1) rather than C(3) substituted bicyclo1,5>hex-3-en-2-ones.Regioselectivities of the acid-catalyzed dienone-phenol rearrangements of C(2) substituted 2,5-cyclohexadienones 11, 45a, and 45b appear to be dependent upon the relative stabilities of carbocations resulting from migration of the C(4) carbomethoxy group.