Toluene → [4-(2-Hydroxyethoxy)phenyl](phenyl)methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of ethylene carbonate (124.6 g; 1.07 eq.), sodium iodide (6.3 g; 0.03 eq.), 4-hydroxybenzophenone (262 g; 1 eq.) and toluene (8.1 g) was heated. At 99° C. a clear solution was obtained. The reaction mixture was heated with reflux condenser to 176° C. over one hour, during which gas evolution occurred. After an additional ½ hour at 176° C., the reaction mixture was cooled to 122° C. and toluene (350 g) and water (24 g) was added. The lower phase was cut and discarded. More water (14 g) was added and the lower phase was again cut and discarded. Water and toluene (95 g in total) was azeotropically removed, reaching a boiling point of 111° C. More toluene (114 g) was added and the product was isolated by filtration at 8° C. In total, 302 g of 4-(2-hydroxyethoxy)benzophenone (94%) was obtained after drying as white crystals (99.8% chromatographic purity).

Provenance & Evidence