p-Toluenesulfonic acid monohydrate → 2-{[(3-Methyl-1H-inden-7-yl)oxy]methyl}morpholine

Participants

Reaction Steps

In 20 ml. of anhydrous toluene was dissolved 100 mg. of 2-(1-hydroxy-1-methyl-4-indanyloxymethyl)morpholine and after adding thereto 10 mg. of p-toluenesulfonic acid monohydrate, the mixture was refluxed for 4 hours. After cooling, the reaction mixture was washed successively with aqueous 3% sodium hydrogencarbonate solution and water, dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue formed was subjected to a silica gel column chromatography (diameter 1.5 cm., height 7 cm.) and from the fraction recovered therefrom using a 98 : 2 mixture of chloroform and methanol as an eluting solution, 69 mg. (yield 74.5%) of sticky 2-(3-methyl-7-indenyloxymethyl)morpholine was obtained. The oxalate of the product had a melting point of 151°-152° C.

Provenance & Evidence