Hydrochloric Acid → 6-(4-Aminophenoxy)-hexanoic acid methyl ester

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Reaction Steps

To a mixture of 6-(4-Amino-phenoxy)-hexanoic acid Hydrochloride 66 (150 grams, 578 mmol), in methanol (3 liters) was passed dry HCl gas at 10° C. for 1 hour and refluxed for 48 hours. Methanol (1.5 liter) was distilled, ice water (1 liter) was added and the pH was adjusted to 7.5 with K2CO3. Crude 67 was extracted into chloroform, washed with 5% NaHCO3 solution, water, dried over Na2SO4 and distilled to give 67 (60 grams, 43.8) as a thick brown syrup. The structure was confirmed with NMR. IHNMR (CDCl3) δ 1.5 (m, 2H, CH2), 1.72 (m, 4H, CH2), 2.34 (t, 2H, CH2), 3.66 (s, 3H, ester), 3.85 (t, 2H, OCH2), 6.56 (d, 2H, Ar), 6.68 (d, 2H, Ar).

Provenance & Evidence