869166-43-8

Upstream product

• 869163-71-3 2-butyl-5-methyl-cyclohex-3-ene-1,2-diol 
• 869162-11-8 acetic acid 5-methyl-2-oxo-cyclohex-3-enyl ester 
• 75337-05-2 4-methyl-2-cyclohexenone 

Downstream Products

• 144791-04-8 2-n-butyl-5-methyl-2,5-cyclohexadiene-1,4-dione 

Relevant academic research and scientific papers

Preparation of 1,4-hydrobenzoquinones by the PCC/SiO2-promoted double oxidation of 3-cyclohexene-1,2-diols

The PCC/SiO2-promoted double oxidation of 3-cyclohexene-1,2- diols, which were easily prepared by the two-step sequence of α-hydroxylation of various conjugated cyclohexenones and the subsequent nucleophilic carbonyl addition of alkyl anions, produced diversely substituted 1,4-hydrobenzoquinones. The Royal Society of Chemistry 2005.

A Potentially General Regiospecific Synthesis of Substituted Quinones from Dimethyl Squarate

A potentially general regiospecific synthesis of benzo- and naphthoquinones is described.This method starts with dimethyl squarate (1) which is converted to the cyclobutenone ketal 3 upon sequential treatment with an organolithium reagent and then BF3 etherate or TFAA in THF/methanol.Treatment of these with a second lithium reagent followed by hydrolysis gives the cyclobutenones 5.Addition of an alkynyl-, alkenyl- or aryllithium agent to 5 followed by hydrolysis of the ketal linkage gives the corresponding 4-alkynyl-, 4-alkenyl- or 4-aryl-4-hydroxycyclobutenones7 - 9, and these readily rearrange to the respective quinones or hydroquinones upon thermolysis in refluxing benzene.In a similar fashion, 15 was employed as a reagent to prepare mono- and disubstituted hydroquinones and quinones.