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Example 2 2-(4-Benzyloxyphenvl')-ethanol[00261] A solution of 2-(4-benzyloxyphenyl)-acetic acid methyl ester (7.8 mmol) in dry ether (5 mL) was added to a suspension of lithium aluminum hydride (15.8 mmol) in 25 mL of dry diethyl ether at 0 0C. The reaction mixture was stirred at ambient temperature overnight, quenched with water, and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate. The solvent was removed under reduced pressure to afford the title compound. Quantitative yield. 1H-NMR (CDCl3): delta 7.28-7.47 (m, 5H); 7.17 (d, J = 8.7 Hz, 2H); 6.95 (d, J- 8.7 Hz5 2H); 5.07 (s, 2H); 3.85 (t, J = 6.6 Hz3 2H); 2.84 (t, J = 6.6 Hz3 2H).
With sodium hydroxide; lithium aluminium tetrahydride; In tetrahydrofuran; water;
(A) A solution of 14.0 g of methyl 4-benzyloxyphenylacetate (7) in THF was slowly added with stirring to a solution of 2.0 g LAH in 500 mL of THF. The mixture was heated at reflux 1 h, cooled with ice, then treated sequentially with 2 mL water, 2 mL 15percent NaOH, and 4 mL of water. The mixture was filtered and the filtrate evaporated to yield 10 g of crystalline 1-benzyloxy-4-(2-hydroxyethyl)benzene (8), m.p. 84°-85° C.
(A) To a suspension of lithium aluminum hydride (10.8 g, 285 mmoles) in Et2 O (300 mL) was very carefully added a solution of methyl 4-(benzyloxy)phenylacetate (6, 72.8 g, 284 mmoles) in Et2 O (200 mL) over 40 minutes. After an additional 30 minutes, ethyl acetate (200 mL) was added, followed by H2 O (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 Et2 O (2*500 mL). The combined extracts were dried over anhydrous Na2 SO4 and evaporated to yield 1-benzyloxy-4-(2-hydroxyethyl)benzene as a white solid, (7, 64.5 g, mp=85° C.). NMR (CDCl3)deltappm: 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
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