1. 10.00g (66.5mmol) of p-tert-butylphenol, 3.50g (116.5mmol) of paraformaldehyde, 0.08g (2mmol) of sodium hydroxide and 60mL of xylene were added to a four-necked flask equipped with an oil-water separator, stirred, and heated to reflux under the protection of N2, refluxed for 4h, precipitating a white solid, left to stand for 1h, pumped and filtered, and the cake was washed twice with 20mL of toluene, petroleum ether, acetone, and water, and dried to give 8.0g of crude product. The filter cake was washed with toluene, petroleum ether, acetone and water 20mL each for 2 times, and dried to obtain 8.0g of crude product. recrystallized with chloroform to obtain 6.9g of bright white crystals with the melting point of 413415 (literature value 411412), the yield was 65%.
2. Weighing p-tert-butyl cup[8]aryl 1 total 2.0g (1.5mmol), phenol 1.2g (12.7mmol) and 2.5g (18.7mmol) of anhydrous aluminum chloride, placed in a 50mL four-necked flask fitted with an N2 protection device, add 30mL of toluene, stirring, through the N2 protection, warming to 45C, and maintain the temperature reaction for 1h. The mixture was poured into a partition funnel, add 50mL of toluene, stirring, and pass N2 protection, and rise to 45C, and keep this temperature reaction for 1h. The reaction was kept at this temperature for 1h. The mixture was poured into a separatory funnel and 50mL of 0.2mol/L hydrochloric acid solution was added. A white colloidal substance appeared in the upper layer of the partition funnel, washed with deionized water to neutral, evaporated the solvent, washed with methanol, filtered, and the crude product was recrystallized with chloroform to give 1.02g of an off-white solid, with a yield of 81%.
