Water → p-(Benzyloxy)phenethyl alcohol

Participants

Reaction Conditions

Reaction Steps

To a suspension of lithium aluminum hydride (10.8 g, 285 mmoles) in Et2O (300 mL) was very carefully added a solution of methyl 4-(benzyloxy)phenylacetate (6, 72.8 g, 284 mmoles) in Et2O (200 mL) over 40 minutes. After an additional 30 minutes, ethyl acetate (200 mL) was added, followed by H2O (500 mL) and the mixture maintained at 0° C. The mixture was then allowed to separate into two phases. The aqueous phase was extracted with Et2O (2×500 mL). The combined extracts were dried over anhydrous Na2SO4 and evaporated to yield 1-benzyloxy-4-(2-hydroxyethyl)benzene as a white solid, (7, 64.5 g, mp=85° C.). NMR (CDCl3)δppm: 7.33(s, 4H); 6.97(q, 4H); 4.97(s, 2H); 3.67(t, 3H); 4.43(t, 3H); 4.27(s, 1H). (Scheme II, Step 2.)

Provenance & Evidence