Hydrochloric Acid → 4-[3-(Methoxymethyl)phenoxy]butyric acid, methyl ester

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A solution of 4-(3-formylphenoxy)butyric acid, ethyl ester (4.72 g) in methanol (25 ml) containing hydrogen chloride (0.35 g) was stirred for 12 hr. at room temperature, then cooled to 0°. Sodium cyanoborohydride (1.26 g) was added and after 30 min., iced water (200 ml) was added and the mixture extracted with ether (2×150 ml). Evaporation of the dried (MgSO4) ethereal extracts gave a pale yellow oil which was distilled (165°/0.8 mm) to give the title compound (3.8 g).

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