56013-05-9

Upstream product

• 79-77-6 (E)-β-ionone 
• 58689-13-7 2-Methyl-2-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]oxirane 
• 105-39-5 chloroacetic acid ethyl ester 

Downstream Products

• 128759-92-2 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,4-pentadienylphosphonic acid,diethyl ester 
• 3899-20-5 ethyl (all-E)-retinoate 
• 128759-88-6 [(2E,4E)-3-Methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienyl]-phosphonic acid diethyl ester 
• 96707-41-4 (+/-)-(E,E,E)-9,10-dihydro-10-hydroxy-retinol 15-acetate 
• 120591-27-7 (+/-)-(E,E,E)-9-(acetyloxy)-3,7-dimethyl-1-<2,6,6-trimethyl-1-cyclohexen-1-yl>-1,5,7-nonatrien-4-one 
• 120591-26-6 (+/-)-(E,E,E)-9-(acetyloxy)-6-hydroxy-3,7-dimethyl-1-<2,6,6-trimethyl-1-cyclohexen-1-yl>-1,7-nonadien-4-one 
• 120591-30-2 Acetic acid (2E,8E)-4-methanesulfonyloxy-3,7-dimethyl-6-oxo-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,8-dienyl ester 
• 84071-80-7 2-Diethoxymethyl-6-[(E)-1-methyl-3-(2,6,6-trimethyl-cyclohex-1-enyl)-allyl]-thiopyran-4-one 
• 84071-79-4 (E)-1,1-Diethoxy-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-non-8-ene-2,5-diyn-4-one 
• 68555-62-4 2-methyl-4-(2,6,6-trimethyl-cyclohex-2-enyl)-crotonaldehyde 
• 130285-78-8 (E)-2-Methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-enal oxime 
• 14398-40-4 (E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)-2-butenal 
• 84071-77-2 2-((E)-5,5-Dibromo-3-methyl-penta-1,4-dienyl)-1,3,3-trimethyl-cyclohexene 
• 98133-84-7 (+/-)-2-methyl-4t-(2.2.6-trimethyl-cyclohexen-⁽⁶⁾-yl)-buten-⁽³⁾-al-⁽¹⁾-thiosemicarbazone 

Relevant academic research and scientific papers

An expedient route to a versatile intermediate for the stereoselective synthesis of all-trans-retinoic acid and beta-carotene

Base-catalyzed isomerization of vinyl phosphonate 5 afforded the corresponding allylic phosphonate (6) as the sole product. Horner-Emmons olefination of ethyl trans-3-methyl-4-oxo-2-butenoate with the ylide derived from 6 concludes a facile synthesis of t

Phosphonate reagent compositions

Novel phosphonate compounds of the formula STR1 are disclosed and claimed, as well as methods for manufacturing the phosphonates from C-14 through C-16 aldehydes. The phosphonate compounds of the present invention can be employed to form 13-cis retinoic acid, retin-A and beta-carotene.

175. The Synthesis of β,γ- and α,β-Unsaturated Aldehydes via Polyene Epoxides

A substitute for the Darzens glycidic ester synthesis for converting unsaturated ketones or aldehydes into the homologated β,γ- or α,β-unsaturated aldehydes employing sulfur ylides is desribed.The carbonyl group is converted into the unsaturated oxirane which is then rearranged to the new aldehyde.High yields of isomerically pure aldehydes are available by this method and the process is of practical importance in the conversion of β-ionone into the β-C14-aldehyde, a key intermediate in the Isler synthesis of vitamin A.The efficient preparation of α- and β-cyclocitral by the novel process is also described.

Preparation of epoxides

Preparation of 1-(2,6,6-trimethyl-1-cyclohexenyl)-3-methyl-3,4-epoxy-but-1-ene from β-ionone by utilizing trimethyl sulfonium chloride in the presence of a phase transfer catalyst and a base; or by utilizing a higher alkyl dimethyl sulfonium salt in the p