Gutsche, C. David’s team published research in Journal of the American Chemical Society in 1968 | CAS: 20921-17-9

Journal of the American Chemical Society published new progress about coumarins dihydro alcoholysis; photoinduced alcoholysis hydrocoumarins. 20921-17-9 belongs to class esters-buliding-blocks, name is Ethyl 4-(2-hydroxyphenyl)butanoate, and the molecular formula is C12H16O3, Name: Ethyl 4-(2-hydroxyphenyl)butanoate.

Gutsche, C. David published the artcileThe photoinduced alcoholysis of 3,4-dihydrocoumarin and related compounds, Name: Ethyl 4-(2-hydroxyphenyl)butanoate, the main research area is coumarins dihydro alcoholysis; photoinduced alcoholysis hydrocoumarins.

The reaction of alcs. with 3,4-dihydrocoumarin and related compounds was studied under ordinary conditions (“”dark solvolysis””) and under photolysis conditions (“”photoinduced solvolysis””). The investigation has revealed the following: the photoinduced alcoholysis of 3,4-dihydrocoumarin to an alkyl β-(2-hydroxyphenyl)propionate can be effected with methanol, ethanol, and isopropanol; tert-butanol, however, fails to react and can be employed as a solvent for the photoinduced reaction with other more reactive alcs.; both the higher and lower homologs of 3,4-dihydrocoumarin undergo photoinduced alcoholysis; the higher homolog, 2-oxo-2,3,4,5-tetrahydrobenzoxepin, reacts in fashion comparable to 3,4-dihydrocoumarin and yields an alkyl γ-(2-hydroxyphenyl)-butyrate, while the lower homolog, 2-oxo-2,3-dihydrobenzofuran, reacts in a different fashion and yields the alkyl ether of 2-hydrobenzyl alc.; the rates of the “”dark solvolyses”” of various 6- and 7-substituted 3,4-dihydrocoumarins are, in accordance with expectations, accelerated by electron-withdrawing groups and decelerated by electron-releasing groups; the photoinduced solvolyses of various 6- and 7-substituted 3,4-dihydrocoumarins show quantum yields which, with one exception, correlate with the pKa* values for the phenol corresponding to the 3,4-dihydrocoumarin. On the basis of these data, it is postulated that the alcoholyses of 3,4-dihydrocoumarins and 2-oxo-2,3,4,5-tetra-hydrobenzoxepin may be examples of photo-induced Fries rearrangements in which an initially produced spirodiketone reacts with the alc. to form the phenolic ester.

Journal of the American Chemical Society published new progress about coumarins dihydro alcoholysis; photoinduced alcoholysis hydrocoumarins. 20921-17-9 belongs to class esters-buliding-blocks, name is Ethyl 4-(2-hydroxyphenyl)butanoate, and the molecular formula is C12H16O3, Name: Ethyl 4-(2-hydroxyphenyl)butanoate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics