55226-78-3

Basic information

• Product Name: methyl (2E)-3-[4-(acetyloxy)phenyl]prop-2-enoate
• Synonyms: methyl 3-[4-(acetyloxy)phenyl]acrylate
• CAS NO: 55226-78-3
• Molecular Formula: C₁₂H₁₂O₄
• Molecular Weight: 220.2213
• Mol File: 55226-78-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 336.2°C at 760 mmHg
• Flash Point: 167.3°C
• Density: 1.171g/cm³
• Vapor Pressure: 0.000114mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: methyl (2E)-3-[4-(acetyloxy)phenyl]prop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2E)-3-[4-(acetyloxy)phenyl]prop-2-enoate(55226-78-3)
• EPA Substance Registry System: methyl (2E)-3-[4-(acetyloxy)phenyl]prop-2-enoate(55226-78-3)

Safety Data

• Hazardous Substances Data: 55226-78-3(Hazardous Substances Data)

Upstream product

• 33527-94-5 4-acetoxyiodobenzene 
• 292638-85-8 acrylic acid methyl ester 
• 27542-85-4 4-acetoxycinnamic acid 
• 77-78-1 dimethyl sulfate 
• 108-59-8 malonic acid dimethyl ester 
• 1384879-86-0 (E)-methyl 3-[2-(4-acetoxystyryl)phenyl]-3-oxopropanoate 
• 123-08-0 4-hydroxy-benzaldehyde 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 7400-08-0 p-Coumaric Acid 
• 7400-08-0 para-coumaric acid 
• 3943-97-3 methyl p-hydroxycinnamate 
• 108-24-7 acetic anhydride 
• 3943-97-3 methyl 4-hydroxycinnamate 

Downstream Products

• 1552301-92-4 2-[4-(4-hydroxyphenyl)-2-oxochroman-6-yl]ethyl methyl carbonate 
• 1552302-02-9 3-(2-hydroxy-5-(2-hydroxyethyl)phenyl)-3-(4-hydroxyphenyl)propanoic acid 
• 10210-17-0 3-(4-hydroxyphenyl)propan-1-ol 
• 922151-70-0 methyl 2-[4-(acetyloxy)phenyl]cyclopropanecarboxylate 
• 3943-97-3 methyl 4-hydroxycinnamate 
• 3943-97-3 methyl p-hydroxycinnamate 
• 20649-40-5 (E)-4-(3-hydroxyprop-1-enyl)phenol 
• 54965-55-8 methyl 3-(4-acetyloxyphenyl)propanoate 
• 120442-73-1 (E)-4-hydroxycinnamyl alcohol 4-O-β-D-glucopyranoside 

Relevant articles and documents

A practical, chemoselective approach to O-methylation of carboxylic acids with dimethyl malonate

A practical and chemoselective method is described for the O-methylation of carboxylic acids. Dimethyl malonate, a low toxic and commercially available compound was found to be an effective methylating reagent for a variety of carboxylic acids affording methyl ester products in good to high yields and with excellent chemoselectivity, without the use of strong bases as additives. A mechanism involving the utilization of potassium bromide is tentatively proposed.

Pd-catalyzed sequential C-C bond formation and cleavage: Evidence for an unexpected generation of arylpalladium(II) species

A Pd(II)-catalyzed reaction engaging alkenyl β-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven β-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.

Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural products descurainin and cartorimine

Reaction of pyranulose 6 with styrenes 12c or 13 and Et3N in CH2Cl2 at 25 °C afforded the [5+2] cycloadducts 14c and 15, which were hydrolyzed to give the natural products 1 and descurainin (2) in 24 and 27% overall yield, respectively. Heating pyranulose 6 with cinnamate ester 21 in the presence of 2,6-di-t-butylpyridine in CH3CN at 175 °C afforded the [5+2] cycloadduct, which was hydrolyzed to give cartorimine (3) in 13% yield.