3',4'-Dibenzyloxy-1-phenyl-2-propanone synthesis

Yield:62932-76-7 83%

Reaction Conditions:

with hydrogenchloride;iron(III) chloride;iron in ethanol;water; for 5 h;Reflux;

Steps:

4.1.2. 1-(3,4-bis(benzyloxy)phenyl)propan-2-one (3)

In a 3 necked round bottomed flask, nitro compound 2 (1.24 g,3.31 mmol), Fe powder (1.11 g, 19.9 mmol, 6 equiv) and FeCl₃ (0.12 mg, 0.76 mmol) were suspended in ethanol (15 mL). To this mixture water (30 mL) and conc HCl (2 mL) were added and the solution was heated at reflux during 5 h. The reaction was cooled down and the pH adjusted to 8 with 40% NH₄OH solution, filteredthrough celite and extracted with EtOAc. The organic phase was washed with water, dried with MgSO₄ and evaporated to give abrown crude, which was purified by column chromatography (SiO₂/hexanes/ethyl acetate) to afford 3 (0.95 g, 83% yield) as brown oil.

References:

Llabrés, Salomé;García-Ratés, Sara;Cristóbal-Lecina, Edgar;Riera, Antoni;Borrell, José Ignacio;Camarasa, Jorge;Pubill, David;Luque, F. Javier;Escubedo, Elena [European Journal of Medicinal Chemistry,2014,vol. 81,p. 35 - 46]