Diethyl Ether → 3-Amino-4-propoxybenzenemethanol

Participants

Reaction Steps

The preparation of part I of Example 1 was repeated with two major changes. The amounts of material employed were increased by a factor of about 10. The reduction in step (e) was carried out differently. To a solution of 1.1 g of lithium aluminum hydride (Alfa Inorganics-Ventron) in 50 ml of scrupulously dried tetrahydrofuran was added dropwise with stirring 2 g of 3-amino-4-n-propoxybenzoic acid in 100 ml of scrupulously dried tetrahydrofuran. The mixture was refluxed for 20 minutes, cooled, diluted with 1 ml of 15% potassium hydroxide and 3 ml of water. Then 150 ml of diethyl ether was added to extract the product. The ether extract was separated, dried and evaporated to yield 1.6 g of the 3-amino-4-n-propoxybenzyl alcohol product, mp 94°-95°.

Provenance & Evidence