19687-18-4

Upstream product

• 470-99-5 isophorol 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 185447-96-5 1-azido-3,5,5-trimethylcyclohex-2-ene 
• 25907-92-0 5,5-dimethyl-3-methylene-cyclohexene 
• 25866-59-5 1,5,5-trimethylcyclohexa-1,3-diene 
• 41169-33-9 3,5,5-trimethylcyclohexa-1,3-diene 
• 127418-17-1 Trimethyl-3,5,5 acetoxy-1 fluoro-3 hydroxy-2 cyclohexane 
• 648857-93-6 3-isopropenyloxy-1,5,5-trimethylcyclohexene 
• 175602-66-1 (3,5,5-trimethyl-2-cyclohexenyl) ethyl ether 
• 50987-46-7 1-methoxy-3,5,5-trimethyl-2-cyclohexene 

Relevant academic research and scientific papers

Synthesis of chiral odoriferous oxy-derivatives of 1,5,5- trimethylcyclohexene

Ten racemic and ten enantiomeric pairs of odoriferous compounds, mainly esters, were obtained from isophorone. The starting material, isophorone was reduced to racemic isophorol, which was resolved in pure enantiomers via the lipase catalyzed esterification. The next steps of syntheses, orthoacetic Claisen rearrangement, reduction of esters, esterification of alcohols or their oxidation were carried out with the racemic and enantiomerically enriched (above 98% ee) compounds. The propionates of isophorol (7, 7a, 7b) and 2-(1,5,5-trimethyl-2-cyclohexen-1-yl)ethanol (10, 10a, 10b) possess the most valuable odoriferous properties, useful for cosmetic and food industries.

Reaction of cyclic allylic acetates with aliphatic alcohols in the presence of cerium(III) chloride

The reactions of selected allylic acetates with methanol, ethanol, n-propyl alcohol, isopropyl alcohol and tert-butyl alcohol in the presence of catalytic amounts of cerium(III) chloride are described. Allylic alkyl ethers, bis-allylic ethers and 1,3-dienes were obtained depending on the structure of the acetates.

The claisen rearrangement in synthesis: Acceleration of the johnson orthoester protocol en route to bicyclic lactones

Catalysis of the Claisen orthoester rearrangement of triethyl orthoacetate and a number of 2-cycloalken-1-ols has been achieved using acidic catalysis and brief microwave thermolysis in DMF. Unlike conventional methods of thermolysis, very high yields of rearranged products are typically obtained in less than ten minutes, and the Claisen products themselves require no further purification. The synthetic utility of the products so obtained is demonstrated in a general synthesis of functionalized bicyclic lactones.

Synthesis of (+/-)-4'-Hydroxy-γ-ionylideneacetic Acids, Fungal Biosynthetic Intermediates of Abscisic Acid

(+/-)-cis and (+/-)-trans-4'-Hydroxy-γ-ionylideneacetic acids (1a and 2a) were synthesized from (+/-)-cis- and (+/-)-trans-4'-acetoxy-γ-cyclocitrals (11a and 11b), respectively, which were obtained by -sigmatropic rearangement of the bromide (9a) prepared from isophorone.Racemic 1a was also synthesized from (+/-)-2,2-dimethyl-4-THPoxy-1-cyclohexanone (14) in 12 steps.