Methyl 11-(p-tert-butylphenoxy)-undecanoate → 11-p-t-Butylphenoxy-1-undecanol

Participants

Reaction Steps

The methyl 11-(p-tert-butylphenoxy)-undecanoate, 3.7 g, 10.6 mmoles, was dissolved in 100 ml dry diethyl ether and added, dropwise, to a stirred slurry of 0.5 g lithium aluminum hydride in 100 ml dry diethyl ether. After one hour the reaction mixture was filtered through Celite and the filtrate was treated with 100 ml 1N hydrochloric acid. The organic layer was removed, dried (MgSO4), and concentrated to a yellow oil, 2.7 g. The oil was chromatographed on 200 g 90 to 200 mesh silica gel (2% MeOH/CH2Cl2 eluent) collecting the product as a white, waxy solid. The solid was recrystallized from warm pentane yielding pure 11-(p-tert-butylphenoxy)-undecanol, 1.1 g, m.p. 39° to 40° C.

Provenance & Evidence