Water → HCID 20684020, compound

Participants

Reaction Steps

To a solution of ethyl 4-[2-(2-methoxyethoxy)ethoxy]benzoate (Step 1, 1.0 g, 3.73 mmol) in 18 mL dry THF was added dropwise a solution of lithium aluminium hydride (1M in THF, 5.6 mL, 5.59 mmol) at 0° C. After the addition was completed, stirring of the reaction mixture was continued for 1 h at rt. Then, 1 g Celite was added, as was 5 mL water with caution. After the addition of sodium hydroxide (1N aq., 2 mL), the precipitate which had formed was removed by filtration. After some washing of the precipitate with ethyl acetate, the organic layer was separated from the filtrate and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo to yield the title compound (710 mg, 84%): 1H NMR (400 MHz, CDCl3) δ 7.28 (d, 2H), 6.90 (d, 2H), 4.61 (s, 2H), 4.14 (t, 2H), 3.86 (t, 2H), 3.72 (t, 2H), 3.58 (t, 2H), 3.39 (s, 3H).

Provenance & Evidence