Chemoselective Esterification of Phenolic Acids in the Presence of Sodium Bicarbonate in Ionic Liquids

Ambika, .; Singh, Pradeep Pratap; Chauhan, S. M. S.

doi:10.1080/00397910701845480

Cited by 21 publications

(7 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Remaining cinnamic acids and α‐phenylcinnamic acid derivatives etc. were prepared by Knoevenagel–Doebner condensation or modified Perkin reaction24–26 in our laboratory. The structures and purity of the synthesized substrates was confirmed by nuclear magnetic resonance (NMR), gas chromatography–mass spectrometry (GC‐MS) and high‐performance liquid chromatography (HPLC) (see online supporting information for characterization of compounds).…”

Section: Methodsmentioning

confidence: 99%

Efficient synthesis of hydroxystyrenes via biocatalytic decarboxylation/deacetylation of substituted cinnamic acids by newly isolated Pantoea agglomerans strains

Sharma

Salwan

et al. 2011

J Sci Food Agric

View full text Add to dashboard Cite

show abstract

Section: Methodsmentioning

confidence: 99%

Efficient synthesis of hydroxystyrenes via biocatalytic decarboxylation/deacetylation of substituted cinnamic acids by newly isolated Pantoea agglomerans strains

Sharma

Salwan

et al. 2011

J Sci Food Agric

View full text Add to dashboard Cite

show abstract

“…However, the relatively polar phenolic acids present low solubility in such systems and the application of microemulsions in industry is hindered by the presence of high concentrations of surfactants. As an alternative, surfactant free microemulsions (Topakas et al 2003;Zoumpanioti et al 2006) and ionic liquids (Katsoura et al 2006;Ambika et al 2008) have been proposed.…”

Section: Introductionmentioning

confidence: 99%

Esterification of phenolic acids catalyzed by lipases immobilized in organogels

et al. 2010

View full text Add to dashboard Cite

Lipases from Rhizomucor miehei and Candida antarctica B were immobilized in hydroxypropylmethyl cellulose organogels based on surfactant-free microemulsions consisting of n-hexane, 1-propanol and water. Both lipases kept their catalytic activity, catalyzing the esterification reactions of various phenolic acids including cinnamic acid 2 derivatives. High reaction rates and yields (up to 94%) were obtained when lipase from C. antarctica was used. Kinetic studies have been performed and apparent kinetic constants were determined showing that ester synthesis catalyzed by immobilized lipases occurs via the Michaelis-Menten mechanism.

show abstract

“…9 Room-temperature ionic liquids (RTILs) are potentially environmentally benign solvents for various organic and biochemical transformations. [9][10][11][12][13][14][15][16][17] The hydrophilicity, hydrophobicity, Lewis acidity, viscosity and density of the ILs can be changed by the choice of organic cation, inorganic anion, and the length of the alkyl chain attached to the ILs. [9][10][11][12][13][14][15][16][17] The ILs have been used in organocatalysis along with Lewis acids, Lewis bases, Brønsted acids and Brønsted bases.…”

Section: Introductionmentioning

confidence: 99%

“…[9][10][11][12][13][14][15][16][17] The hydrophilicity, hydrophobicity, Lewis acidity, viscosity and density of the ILs can be changed by the choice of organic cation, inorganic anion, and the length of the alkyl chain attached to the ILs. [9][10][11][12][13][14][15][16][17] The ILs have been used in organocatalysis along with Lewis acids, Lewis bases, Brønsted acids and Brønsted bases. [9][10][11][12][13][14][15][16][17] The reactions of cytochrome P450 in ILs have been studied in recent years.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective epoxidation of electron rich and electron deficient olefins catalyzed by meso-tetraarylporphyrin iron(iii) chlorides in imidazolium ionic liquids

2012

Self Cite

View full text Add to dashboard Cite

The oxygenation of substrates containing both electron rich and electron deficient olefins (1a-b) catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides [TAPFe(III)Cl] with H 2 O 2 gave epoxides at both electron rich and deficient olefin (2a-b, 3a-b), while with iodosyl benzene (PhIO) gave the epoxides only at electron rich olefin (3a-b) in imidazolium ionic liquids (ILs). Further reaction of 2a-b with sodium hydroxide in methanol gave 4a-b by base catalysed rearrangement of enedione epoxides. Similar reaction of 4a-b with H 2 O 2 or PhIO gave the major epoxides of electron deficient olefins and electron rich olefins. The ferric peroxy anions (TAP-Fe III -OO À ) are effective intermediates in the epoxidation of electron deficient olefins, whereas the high valent oxoferrylporphyrin p-cation radicals (TAP-Fe IV QO + ) are involved in the epoxidation of electron rich olefins. The ILs provide the special microenvironments by the interactions of cations and anions, in which the generation of the active intermediates from TAPFe(III)Cl/[Bmim] [PF 6 ] and monooxygen donors could be accelerated significantly.

show abstract

Chemoselective Esterification of Phenolic Acids in the Presence of Sodium Bicarbonate in Ionic Liquids

Cited by 21 publications

References 26 publications

Efficient synthesis of hydroxystyrenes via biocatalytic decarboxylation/deacetylation of substituted cinnamic acids by newly isolated Pantoea agglomerans strains

Efficient synthesis of hydroxystyrenes via biocatalytic decarboxylation/deacetylation of substituted cinnamic acids by newly isolated Pantoea agglomerans strains

Esterification of phenolic acids catalyzed by lipases immobilized in organogels

Chemoselective epoxidation of electron rich and electron deficient olefins catalyzed by meso-tetraarylporphyrin iron(iii) chlorides in imidazolium ionic liquids

Contact Info

Product

Resources

About