1,4-dihexylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Nitrogen was introduced into a flask (250 ml), and 10 ml of anhydrous diethyl ether was added, and 15 g of magnesium was added, and stirred. Hexyl bromide (0.61 mole) of 100 g mixed with 50 ml of diethylether was poured into a dropping funnel, and the mixture therein was slowly added into the flask over 1 hour. The reaction was carried out at 45° C. for 3 hours. The reaction product, Grignard, was poured into a dropping funnel. To the reactant was slowly added a mixture of 42 g of 1,4-dichlorobenzene (0.29 mol), 0.3 g of NiCl2 and 80 ml of diethylether, and the reaction was carried out at room temperature for 24 hours to obtain solid reaction product. 6 N HCl was slowly added so as to neutralize the solid reaction product, the product was extracted with diethyl ether and dried with anhydrous MgSO4, and the reaction product was separated by vacuum distillation (122° C./0.1 mmHg). The structure analysis of the compound was confirmed by 1H-NMR, which was shown in FIG. 3. was added was poured into a dropping funnel the mixture therein was slowly added into the flask over 1 hour The reaction product, Grignard, was poured into a dropping funnel To the reactant was slowly added the reaction was carried out at room temperature for 24 hours to obtain solid reaction product the solid reaction product the product was extracted with diethyl ether dried with anhydrous MgSO4 the reaction product was separated by vacuum distillation (122° C./0.1 mmHg)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2 L round-bottomed flask is charged with 1,4-dichlorobenzene (118 g, 0.80 mol), [1,3 -bis(diphenylphosphino)propane]Ni(II) chloride (500 mg, 0.9 mmol), and dry ether (600 mL). The mixture is cooled to 0° C. and a 2 M solution of n-hexylmagnesium bromide in ether (1 L) is added dropwise. The cooling bath is removed, and the solution is slowly heated to reflux and allowed to boil for 24 h. The mixture is cooled to 0° C. and diluted with water (50 mL) and then with a 2 M aqueous hydrochloric acid solution (500 mL). The aqueous layer is separated, extracted with ether (2×200 mL), and the combined organic layers are washed with water (100 mL) and dried over magnesium sulfate. The solvent is removed in vacuo and the product is purified by distillation. The cooling bath is removed the solution is slowly heated to reflux The mixture is cooled to 0° C. diluted with water (50 mL) The aqueous layer is separated extracted with ether (2×200 mL) the combined organic layers are washed with water (100 mL) dried over magnesium sulfate The solvent is removed in vacuo the product is purified by distillation