Phenol, 4,4'-cyclododecylidenebis- synthesis

Yield:29651-54-5 77.04 g

Reaction Conditions:

Stage #1: phenolwith sulfuric acid at 80; for 1 h;
Stage #2: cyclododecanonewith 1-dodecylthiol at 30 - 65; under 9.75098 Torr; for 52 h;Reagent/catalyst;Temperature;

Steps:

1-6 Example 4

258.19 g (2.74 mol) of phenol and 13.72 g (0.137 mol) of 98% sulfuric acid were charged into a 500 ml glass reaction vessel equipped with a stirrer, a condenser and a thermometer, and the temperature was raised to 80 ° C. After stirring at the same temperature for 1 hour, 50.09 g (0.275 mol) of cyclododecanone at 60 ° C.,5.54 g (0.0274 mol) of n-dodecylmercaptan was added and reacted at 65 ° C. while removing water at 1.3 kPa until the remaining amount of cyclododecanone reached 50% of the initial charge amount.After recovering pressure to normal pressure with nitrogen gas, it was cooled to 30 ° C. and left to stand at the same temperature for 52 hours.0.15 g of the solidified reaction mass was scraped off, and the reaction mass was analyzed by gas chromatography. As a result, the remaining amount of cyclododecanone was 1% of the initially charged amount, and 1, 1-bis (4-hydroxy Phenyl) cyclododecane (the molar ratio to the initially charged amount of cyclododecanone) was 90.2%. Toluene and ion exchanged water were added to the obtained reaction mass, neutralized with sodium hydroxide, and then washed with ion exchanged water. The obtained organic layer was cooled as it was, the precipitated crystal was taken out by filtration and dried. The obtained crystals were recrystallized from methanol water, taken out by filtration and dried to obtain 77.04 g (0.219 mol, yield 79.5 mmol) of 1, 1-bis (4-hydroxyphenyl) cyclododecane %, HPLC purity 100%) was obtained

References:

JP2015/51935,2015,A Location in patent:Paragraph 0031-0040