Dimethyl Sulfoxide → 2-(3,7-dimethyloctoxy)-5-methoxyterephthalaldehyde

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Reaction Conditions

Reaction Steps

A 4 l four-neck flask with condenser, precision glass stirrer, internal thermometer and dropping funnel was initially charged with 176.8 g (1.39 mol) of oxalyl chloride and 450 ml of dichloromethane and cooled to −50° C. To this was added dropwise within 45 min a solution of 253.5 g (3.43 mol) of DMSO in 450 ml of dichloromethane. The mixture was stirred for a further 30 min. A solution of 183.8 g (0.57 mol) of 2,5-bis(hydroxymethyl)-1-(3,7-dimethyloctyl-oxy)-4-methoxybenzene in 500 ml of dichloromethane was then added dropwise over 2.5 h. After addition of 100 ml, a white precipitate formed. After addition of 400 ml of the solution, a further 500 ml of dichloromethane were added. After the addition had been completed, the mixture was stirred for a further 15 min, then 151.8 g (1.5 mol) of triethylamine were added dropwise within 1 h. The mixture was allowed to come to room temperature overnight, then 1500 ml of water were added and the mixture was stirred for 0.5 h. The phases were separated, and the aqueous phase was extracted with 2×300 ml of water. The combined organic phases were washed with 1×500 ml of water and dried over Na2SO4, and the solvent was removed under reduced pressure. 175.6 g (58% of theory) of the product were obtained, which was used for the next stage without further purification and without further characterization.

Provenance & Evidence