133532-17-9

Upstream product

• 541-47-9 3-Methylbutenoic acid 
• 108-39-4 3-methyl-phenol 
• 35660-94-7 (E)-2-methylbut-2-enoyl chloride 
• 3350-78-5 3,3-Dimethylacryloyl chloride 

Downstream Products

• 69687-88-3 (±)-2,7-dimethyl-4-chromanone 
• 110411-30-8 2,2,7-trimethylchroman-4-one 
• 105640-09-3 3,4-dihydro-4,4,7-trimethylcoumarin 
• 142337-65-3 1-(2-hydroxy-4-methylphenyl)-3-methyl-2-buten-1-one 
• 108-39-4 3-methyl-phenol 

Relevant academic research and scientific papers

Bismuth(III) triflate catalyzed tandem esterification–Fries–oxa-Michael route to 4-chromanones

An efficient tandem reaction approach is described to prepare 4-chromanones from electron-rich phenols and 3,3-dimethylacrylic acid or trans-crotonic acid in boiling toluene using 20?mol?% bismuth(III) triflate as the catalyst. The reaction is also successful from the corresponding aryl esters of each of these acids under the same conditions. The procedure is convenient to perform, and 25–90% yields of products are realized following chromatography. A range of substrates is included (14 substrates for each acid) to help define the scope of the process. Additional experiments are reported, which confirm that the sequence of events involves (1) esterification, (2) Fries rearrangement and (3) oxa-Michael ring closure.

Expeditious photochemical reaction toward the preparation of substituted chroman-4-ones

A facile photochemical preparation of 5-, 6-, and 7-substituted chroman-4-ones from aryl 3-methyl-2-butenoate esters is described. The two-phase base-catalyzed method relies upon two consecutive processes in one-pot reaction through a photo-Fries rearrangement and a based-catalyzed intramolecular oxa-Michael addition to afford the desired products.

ON THE REACTION OF SUBSTITUTED PHENOLS AND 3-METHYLBUT-2-ENOIC ACID. A COMPARATIVE STUDY

A systematic and comparative study of the reaction of a series of substituted phenols and 3-methylbut-2-enoic acid in zinc chloride/phosphorus oxychloride and aluminum chloride/phosphorus oxychloride reveals that the formation of phenolic esters and 2,2-dimethyl-4-chromanones is strongly influenced by the substituents, their popsition on the aromatic ring of the starting phenols.Based on our study, a mixed Friedel-Crafts and Fries rearrangement mechanism is in operation in these reactions.

Chroman esters of phenols and benzoic acids having retinoid-like activity

Retinoid like activity is exhibited by compounds of the formula STR1 wherein the R 1 -R 7 groups are independently H or straight chain or branched chain lower alkyl or cycloalkyl of 1 to 6 carbons; X symbolizes an ester or thioester linkage, Y is cycloalk

Acetylenes disubstituted with a phenyl group and a 2-substituted chromanyl or thiochromanyl group having retinoid-like activity

Retinoid-like activity is exhibited by compounds of the formula STR1 where X is S, O; R1, R2 and R3 are hydrogen or lower alkyl; R4 and R5 are hydrogen or lower alkyl with the proviso that R4/su