Sodium borohydride → 1-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-(4-carboxyphenoxy)ethanol

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Reaction Steps

2.1 g (5 mmol) of 1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-(4-ethoxycarbonylphenoxy)ethanone (from Example 5) in 100 ml of tetrahydrofuran/methanol (2:1) were stirred with 0.4 g (10 mmol) of sodium borohydride at room temperature for 30 min; the reaction solution was poured into saturated brine and extracted with ethyl acetate; the extracts were washed with water, dried over magnesium sulfate and evaporated to provide an oily residue which was subjected to alkaline hydrolysis as described in Example 6 and yielded after appropriate working up 1.4 g of the title compound; melting point (cyclohexane): 160°-162° C.

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