Hydrochloric Acid → Tetradecanoic acid, 2-[4-[(butylsulfonyl)amino]phenoxy]-

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Reaction Steps

92 g (0.19 mol) of ethyl-α-[p-butylsulfonylaminophenoxy]tetradecanoate (Intermediate II) obtained in Step B, and 500 ml of ethyl alcohol were placed in a 3-necked flask. A solution of 20 g of sodium hydroxide (dissolved in a minimum amount of water) was added with good stirring. The reaction mixture was refluxed for 3 hours, allowed to cool to room temperature, poured into ice water and acidified with concentrated hydrochloric acid. The oil was extracted with ether, washed with water and saturated sodium chloride solution. The ether was removed under vacuo to give a gummy solid. After trituration with ligroine (boiling point: 35°-60° C.), the solid was collected. Yield was 50 g of Intermediate III, m.p. 80°-82° C. TLC analysis (benzene) showed one product.

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