2,6-Di-tert-butyl-4-methylphenol → HCID 86759483, compound

Participants

Reaction Steps

2.54 g of (1R,2R)-N-(2-diphenylphosphanylbenzyl)cyclohexane-1,2-diamine hydrochloride (6 mmol) are combined with 100 ml of methylene chloride and 100 ml of saturated sodium hydrogen carbonate solution. Once the phases have separated, the aqueous phase is extracted twice more with methylene chloride and the combined organic phases are washed with saturated sodium chloride solution. Drying is then performed with magnesium sulfate and the solvent removed in a rotary evaporator. After drying under a high vacuum, 1.71 g of (1R,2R)-N-(2-diphenylphosphanylbenzyl)cyclohexane-1,2-diamine (4.4 mmol) are obtained as an air-sensitive clear oil. This is dissolved in 250 ml of absolute ethanol under a protective gas atmosphere in a three-necked flask equipped with a reflux condenser. Once combined with 1.85 g of 2-diphenylphosphanyl-5-(4-vinylbenzyloxy)benzaldehyde (4.4 mmol) and 96 mg of 2,6-di-tert.-butyl-p-cresol (0.4 mmol), the reaction solution is refluxed for 1 hour under protective gas. The reaction mixture is then left to cool and combined with 1.66 g (44 mmol) of sodium hydridoborate. After 3 hours, the reaction is quenched by adding 50 ml of acetone and the solvent is completely removed in a rotary evaporator. The resultant residue is stirred with 100 ml of saturated ammonium hydrochloride solution and 100 ml of methylene chloride until completely dissolved. The aqueous phase is extracted twice more with methylene chloride and the combined organic phases are washed with water and saturated sodium chloride solution. Drying is then performed with magnesium sulfate and the solvent removed. After drying under a high vacuum, 2.83 g of the product, corresponding to a yield of 79%, are obtained as a white mass (stabiliser content according to NMR 9.4%).

Provenance & Evidence