89127-43-5

Basic information

• Product Name: Benzoic acid, 2-methyl-, 4-methoxyphenyl ester
• CAS NO: 89127-43-5
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Mol File: 89127-43-5.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-methyl-, 4-methoxyphenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-methyl-, 4-methoxyphenyl ester(89127-43-5)
• EPA Substance Registry System: Benzoic acid, 2-methyl-, 4-methoxyphenyl ester(89127-43-5)

Safety Data

• Hazardous Substances Data: 89127-43-5(Hazardous Substances Data)

Upstream product

• 118-90-1 ortho-methylbenzoic acid 
• 73686-46-1 2-methylbenzoic acid 2-pyridinyl ester 
• 150-76-5 4-methoxy-phenol 
• 933-88-0 ortho-toluoyl chloride 

Downstream Products

• 117593-65-4 1-<2-<(4-methoxyphenoxy)carbonyl>benzyl>-4-(aminocarbonyl)pyridinium bromide 
• 117593-63-2 1-<2-<(4-methoxyphenoxy)carbonyl>benzyl>-3-(aminocarbonyl)pyridinium bromide 
• 959101-83-8 2-Bromomethyl-benzoic acid 4-methoxy-phenyl ester 

Relevant articles and documents

Transesterification of (hetero)aryl esters with phenols by an Earth-abundant metal catalyst

Readily available and inexpensive Earth-abundant alkali metal species are used as efficient catalysts for the transesterification of aryl or heteroaryl esters with phenols which is a challenging and underdeveloped transformation. The simple conditions and the use of heterogeneous alkali metal catalyst make this protocol very environmentally friendly and practical. This reaction fills in the missing part in transesterification reaction of phenols and provides an efficient approach to aryl esters, which are widely used in the synthetic and pharmaceutical industry.

EFFECT OF NEIGHBORING PYRIDINIUM GROUPS ON THE BASIC HYDROLYSIS OF ARYLBENZOATE ESTERS

Arylbenzoate esters with a quaternary pyridinium group ortho to the ester function exhibit enhanced reactivity towards basic hydrolysis relative to their para analogs in the order pyridinium 4-aminocarbonylpyridinium 3-aminocarbonylpyridinium 3-aminocarbonylquinolium.In contrast, a trimethylammonium group in the ortho position shows a decelerating effect relative to the para analog.It is concluded that the catalytic effect of a neighboring pyridinium group is based upon interaction of the negatively charged transition state of ester hydrolysis with the electron deficient ?-system of the pyridinium ring.For the p-methoxyphenolate ester containing the 3-aminocarbonylpyridinium group in the ortho position this interaction leads to a change in mechanism from rate limiting hydroxide ion attack to hydroxide ion catalyzed expulsion of the leaving group as became apparent from deviation of the Hammett plot and second-order dependence on OH(1-) concentration.For the p-nitrophenolate ester it was observed that decrease of the solvent polarity by addition of dioxane results in an increase of the rate of hydrolysis and a marked increase of the neighboring group effect.