Monobenzone → Methyl 2-[(4-{2-[4-(benzyloxy)phenoxy]ethyl}phenoxy)methyl]benzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 2-{[4-(2-hydroxyethyl)phenoxy]methyl}benzoate (1 g, 3.49 mmol), 4-(benzyloxy)phenol (0.7 g, 3.49 mmol) and triphenylphosphine (1.01 g, 3.84 mmol) was added to a dry round bottomed flask fitted with a septum. N2 was flushed through the flask for 5 minutes followed by the addition of dry toluene (30 ml) and diisopropylazo-dicarboxylate (0.78 g, 3.84 mmol). The reaction mixture was stirred at 55° C. overnight. The solvent was removed by evaporation and the crude material was purified by preparative HPLC (started with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). After removing the solvent by evaporation, 0.7 g of methyl 2-[(4-{2-[4-(benzyloxy)phenoxy]ethyl}phenoxy)methyl]benzoate was isolated (yield 42.8%).

Provenance & Evidence