34 ml 34 mmol solid 4 8 dehydrobenzo 1 2 b 4 5 b u2032 dithiophene 4 8 dione 2 50 grams 11 4 mmol was added in one portion and the reaction was heated to 60 u00b0 c under an argon atmosphere after 90 minutes the heating bath was removed and the reaction was cooled to room temperature and carefully quenched with water 20 ml the reaction was treated with a solution of tin ii chloride 12 91 grams 68 1 mmol in 10 vol hydrochloric acid solution 30 ml and was heated to 60 u00b0 c after 18 hours the heating bath was removed and the reaction was cooled to room temperature the layers were separated and the organic layer was dried using mgso 4 filtered and concentrated using a rotary evaporator the crude product was passed through a short sio 2 plug using hexanes as eluent and the product was recrystallized from hexanes yielding 4 8 didodecylbenzo 1 2 b 4 5 b u2032 dithiophene as a white solid 1 7 grams 28 yield the structure was confirmed by 1 h and 13 c nmr spectroscopy in a 500 ml round bottomed flask 4 8 dehydrobenzo 1 2 b 4 5 b u2032 dithiophene 4 8 dione 2 50 grams 11 4 mmol was suspended in anhydrous tert butylmethyl ether 150 ml the suspension was treated dropwise with a 1m solution of dodecylmagnesium bromide 45 4.