Succinic anhydride → 4-[3,5-Dimethyl-4-methoxyphenyl)butanol

Participants

Reaction Steps

A mixture of 2,6-dimethylanisole (4.45 g), succinic anhydride (4.80 g) and aluminum chloride (4.70 g) in toluene (60 ml) is stirred for 2.7 hr at 20°-25°. A 100 ml aliquot of methylene chloride is added for solubility. The reaction is run for 6 hr. The reaction is poured onto ice and extracted with methylene chloride-isopropanol. The organic phase is washed with saline, dried over sodium sulfate, concentrated and dried under reduced pressure overnight to give a solid. This material is stirred with borane-methyl sulfide complex (1.0M, 38 ml) in THF at 20°-25° for 24 hr. Aqueous sodium bicarbonate, methylene chloride and water are added. The ketoalcohol product is combined with other partly reduced materials and treated with borane-methyl sulfide complex in excess in methylene chloride for 72 hr. It is important that the ketoacid Friedel Crafts adduct should be reduced exhaustively with excess borane-methyl sulfide complex.

Provenance & Evidence