138100-91-1

Upstream product

• 591-51-5 phenyllithium 
• 106-51-4 p-benzoquinone 
• 42860-77-5 4-hydroxy-4-phenyl-cyclohexa-2,5-dienone 

Downstream Products

• 138100-97-7 trans-3,6-dimethoxy-3,6-diphenylcyclohexa-1,4-diene 
• 138100-96-6 cis-3,6-dimethoxy-3,6-diphenylcyclohexa-1,4-diene 

Relevant academic research and scientific papers

Stereoselective Two-Step Chemical Preparation of 1,4-Dialkyl-1,4-dimethoxycyclohexa-2,5-dienes

The reaction of p-benzoquinone (1) with several organolithium compounds (methyl-, ethyl-, n-butyl-, phenyllithium) led, after hydrolysis with water, to the corresponding crude diols 4, which were successively treated with sodium hydride and methyl iodide yielding the expected 1,4-dialkyl-1,4-dimethoxycyclohexa-2,5-dienes 2a-d in a stereoselective manner.The use of a tandem process with two different organolithium reagents followed by methylation by the same procedure yielded stereoselectively the mixed 1-alkyl-4-alkyl' derivatives 2e,f.

REACTIONS OF ORGANOLITHIUM REAGENTS WITH p-BENZOQUINONES AND CYCLOHEXADIENONS, SYNTHESIS OF 4-ALKYL-4-HYDROXYCYCLOHEXA-2,5-DIEN-1-ONES AND 1,4-DIALKYLCYCLOHEXA-2,5-DIENE-1,4-DIOLS.

Addition of organolithium reagents to p-benzoquinones in ether gives the corresponding 4-alkyl-4-hydroxycyclohexa-2,5-dien-1-ones.Addition of excess of the reagent to the p-benzoquinones, or to the 4-alkyl-4-hydroxycyclohexa-3,5-dien-1-ones, in tetrahydrofuran, gives the corresponding dialkylcyclohexa-2,5-diene-1,4-diols.