One-pot synthesis of 2,2'-Arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) by electrochemical method

Document Type : Original Article



2,2'-Arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives are important biologically active compounds, which can be evaluated as tyrosinase inhibitors. They are important intermediates in the synthesis of xanthenes that are known as an important class of heterocyclic compounds with biological and therapeutic properties. Several methods have been employed for the preparation of 2,2'-Arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives, including the use of molecular iodine, ultrasonic and microwave irradiation. Some of these methods however, involve harsh reaction conditions. Therefore, further improvement toward milder reaction conditions and higher yields is required. In recent years, the advance of electro-synthesis have attracted organic chemists for having advantages such as short reaction time, high yields with easy work-up and do not require the use of harsh conditions such as high temperature and expensive reagents. In this study, we report a convenient and facile synthesis of 2,2'-Arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) based on electro-catalytic transformation of aldehyde and dimedone in an undivided cell containing an iron electrode as the cathode and a Pt electrode as the anode at a constant current in the presence of potassium bromide as an electrolyte at room temperature.