Photoremovable protecting groups (PPGs), when bound covalently to compounds, provide spatial and temporal control of the release from the protecting groups. PPGs enable researchers to control the release of bioactive compounds, such as neurotransmitters, in living tissue. Like their name states, PPGs are removed by the action of absorbed light. The PPG used in this study is p-hydroxyphenacyl (pHP) because of its unique properties such as high quantum yields, a biologically inert byproduct, and quantitative yield of deprotected product. Most molecules protected by the pHP ligand have an acidic moiety such as a carboxylic, phosphoric or sulfonic acid functional group. Many biological compounds of interest, however, lack this sort of relatively acid moiety, and caging of much less acidic moieties such as phenols is currently under study. The main goal of the study is to develop a method to synthesize and deprotect caged phenols. Once the phenols are synthesized, their photochemical properties are measured in order to determine the viability of the chemistry. A three-step procedure was employed to synthesize  2’-phenoxy-4-hydroxyacetophenone. A solid-state organic reaction using the organic base 1,4-diazabicyclo[2.2.2]octane (DABCO) was studied as an alternative method for the final step.

Synthesis of 2’-phenoxy-4-hydroxyacetophenone

249th National Meeting (2015)

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