Lithium Hydroxide → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid

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Reaction Steps

4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid was prepared as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid. 4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester (1.6 g, 4.08 mmol, 1 eq.) in 30% aqueous THF was treated with lithium hydroxide (0.29 g, 12.24 mmol, 3 eq.). When complete, the reaction was worked up as described and the resulting oil purified via silica gel flash chromatography using 50% EtOAc in hexane as the mobile phase. Fractions containing the product were pooled and the solvent removed in vacuo leaving 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid (1.44 g, 97% yield) as an orange oil.

Provenance & Evidence