133532-17-9

Basic information

• Product Name: 3'-methylphenyl 3-methylbut-2-enoate
• Synonyms: 3'-methylphenyl 3-methylbut-2-enoate
• CAS NO: 133532-17-9
• Molecular Weight: 190.242
• Mol File: 133532-17-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3'-methylphenyl 3-methylbut-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-methylphenyl 3-methylbut-2-enoate(133532-17-9)
• EPA Substance Registry System: 3'-methylphenyl 3-methylbut-2-enoate(133532-17-9)

Safety Data

• Hazardous Substances Data: 133532-17-9(Hazardous Substances Data)

Upstream product

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

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.

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.

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