Dichloromethane → 2-[(4-Benzoylphenoxy)methyl]oxirane

Participants

Reaction Conditions

Reaction Steps

4-Hydroxybenzophenone (10.0 g; 50.5 mmol) was dissolved in epichlorohydrine (50 mL). Tetraethylammonium bromide (0.1 g; 0.48 mmol) was added and the reaction mixture was heated to 100° C. for 30 h under reflux. Near quantitative conversion of the starting material was confirmed by TLC. The reaction mixture was cooled to 30° C. and 50% aqueous NaOH (6.06 g, 75.7 mmol) was added dropwise to the vigorously stirred solution. The stirring was continued for a further 3 h at this temperature. The reaction mixture was then poured into methylene chloride (200 mL) and washed with water (3×50 mL). The organic layer was separated, dried over magnesium sulfate, filtered and evaporated to dryness. The crude product was recrystallised from methyl tert-butyl ether to yield 2-(4-benzoylphenoxymethyl)oxirane (10.66 g; 83% yield) as a white crystalline solid.

Provenance & Evidence