Methylparaben → N,N-Diisopropyl-3-[(5-methoxycarbonyl)-2-hydroxy)phenyl]-3-phenyl-propylamine

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Reaction Conditions

Reaction Steps

Methyl 4-hydroxy-benzoate (52.0 g, 340 mmols) is suspended in methanesulfonic acid (90 ml) in a round-bottom flask under inert atmosphere, and the mixture is heated to a temperature of 50-55° C. 3-Diisopropylamino-1-phenyl-propan-1-ol (20.0 g, 85.0 mmols) is slowly added thereto in about 2 hours and the hot mixture is reacted for 5-6 hours. The mixture is cooled to room temperature and slowly poured into ice/water (200 g) under strong stirring. The product is extracted with dichloromethane (200 ml) and the organic phase is washed with a 10% sodium hydroxide solution (2×100 ml), then with an ammonium chloride aqueous solution to neutral pH. 28.9 g of product are obtained in 92% yield.

Provenance & Evidence