c acid (I) was obtained by method [5]. The alkylation of I by butyl iodide in NaOH aqueous solution under interphase catalysis conditions did not yield positive resutls. We did succeed in alkylating I in acetone in the presence of potassium carbonate by the method in [ii]. However, this resulted in the formation of alkylation products both for the phenol hydroxyl and the carboxyl group. Complete alkylation of the phenol group required an excess of butyl iodide of not less than 3 moles per mole of I. This resulted in a good yield of the butyl ester of 2-butoxy-4-chlor~benzoic acid (II). Alkylation of the ethyl ester of 4-chlorosalicyli c acid (III), obtained by the method in [15] with butyl iodide under similar conditions produces a good yield of the ethyl ester of 2-butoxy-4-chlorobenzoic acid (IV) and makes it possible to halve the consumption of butyl iodide and potassium carbonate. Alkaline hydrolysis of the esters of II and IV yielded 2-butoxy-4-chlorobenzoic acid (V). The structure of II, IV, and V was confirmed by IRspectroscopy and element analysis. Compounds II, IV, and V had the following absorption bands in the IR-spectra (at cm-1): II - 1730, 1130 (COOR), 1230, 1072 (Ar-<)-C); IV - 1730, 1290, 1132 (COOR), 1235, 1072 (Ar-<}-C); V - 3090, 1668, 1440, 1290 (COOH), 1240, 1080 (Ar-O-C). The structure of V was also confirmed by its titration with 0.i N NaOH in ethanol with phenolphthalein as the indicator. of compound V by chlorosulfonic acid either in chloroform or without a solvent at 65  5~ is accompanied by the splitting of the simple ester bond and the substitution of the carboxyl gorup. This is confirmed by the formation of butyl alcohol and CO 2. We were not able to extract individual sulfochlorides from the resultant oily product which contained no less than three compounds, according to TLC data. When the mixture was treated with ammonia sulfochlorides, the result was a mixture of sulfamides from which we obtained low yields of 4-chloro-5-sulfamoylsalicylic acid (VI) and 2-butoxy-4-chlor-5-sulf~moylbenzoic acid (VII). We also observed the cleavage of the simple ester bond and the subsequent formation of sulfochloride mixtures when esters II and IV were sulfochlorinated under similar conditions. This difficulty could not be overcome by lowering the reaction temperature. Therefore, the sulfochlorination of compound V or its esters by chlorosulfonic acid in order to obtain compound VII is of no preparative significance.

中文翻译：

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4-氯水杨酸衍生物的合成及利尿作用

c酸(I)通过方法[5]获得。在相间催化条件下，碘代丁烷在 NaOH 水溶液中对 I 进行烷基化没有产生阳性结果。我们确实通过 [ii] 中的方法在碳酸钾的存在下成功地在丙酮中将 I 烷基化。然而，这导致酚羟基和羧基的烷基化产物的形成。酚基的完全烷基化需要每摩尔 I 不小于 3 摩尔的过量碘化丁基。这导致 2-丁氧基-4-氯-苯甲酸 (II) 的丁酯的良好收率。4-氯水杨酸乙酯(III)的烷基化，通过[15]中的方法与丁基碘在类似条件下获得的2-丁氧基-4-氯苯甲酸(IV)的乙酯产率高，并且可以将丁基碘和碳酸钾的消耗量减半。II和IV的酯的碱水解产生2-丁氧基-4-氯苯甲酸(V)。II、IV 和 V 的结构通过红外光谱和元素分析得到证实。化合物 II、IV 和 V 在红外光谱中具有以下吸收带（在 cm-1 处）：II - 1730、1130 (COOR)、1230、1072 (Ar-<)-C)；IV - 1730, 1290, 1132 (COOR), 1235, 1072 (Ar-<}-C)；V - 3090、1668、1440、1290 (COOH)、1240、1080 (Ar-OC)。以酚酞为指示剂，用 0.1 N NaOH 的乙醇溶液滴定，也证实了 V 的结构。在氯仿中或无溶剂下，在 65 ℃下用氯磺酸反应化合物 V 的反应。5~伴随着简单酯键的分裂和羧基的取代。丁醇和 CO 2 的形成证实了这一点。根据 TLC 数据，我们无法从含有不少于三种化合物的所得油状产品中提取单个硫氯化物。当混合物用氨磺酰氯处理时，结果是磺酰胺的混合物，我们从中获得了低收率的 4-氯-5-氨磺酰基水杨酸 (VI) 和 2-丁氧基-4-氯-5-磺基-甲基苯甲酸（七）。我们还观察到，当酯 II 和 IV 在类似条件下被磺氯化时，简单酯键断裂并随后形成磺氯化物混合物。这个困难不能通过降低反应温度来克服。因此，化合物V或其酯类用氯磺酸磺氯化得到化合物VII没有制备意义。