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With hydrogenchloride; sodium hydroxide In methanol
2 Preparation of 3-hydroxy-4-(hydroxymethyl) benzoic acid
EXAMPLE 2 Preparation of 3-hydroxy-4-(hydroxymethyl) benzoic acid 316 mg of methyl 3-hydroxy-4-(hydroxymethyl) benzoate prepared as described in Example 1 was dissolved in 1 ml of methanol, to which was then added 5 ml of 1 N aqueous sodium hydroxide. The mixture was allowed to stand at room temperature for 1.5 hours to effect the saponification. Thereafter, the reaction mixture was diluted with water, admixed with 5 ml of 1 N hydrochloric acid and then extracted with ethyl acetate. The extract was evaporated under reduced pressure to remove the solvent, yielding 272 mg (93%) of the desired product. Recrystallization from a mixture of benzene-ethanol gave 154 mg of the titled compound as colorless crystals. Melting point: 173.5°-174.5° C. (with decomposition)
3-n-hexyloxy-4-n-hexyloxymethylbenzoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium hydroxide; potassium hydrogen sulphate In tetrahydrofuran; <i>N</i>-methyl-acetamide; methanol; chloroform; water
14 Preparation of 3-n-hexyloxy-4-n-hexyloxymethylbenzoic acid
EXAMPLE 14 Preparation of 3-n-hexyloxy-4-n-hexyloxymethylbenzoic acid Anhydrous dimethylformamide (10 ml) was added to 100 mg of 3-hydroxy-4-hydroxymethylbenzoic acid and 95.2 mg of sodium hydride in oil, followed by addition of 0.33 ml of n-hexyl bromide. The resultant mixture was then stirred at room temperature for 24 hours. n-Hexyl bromide (0.10 ml) was then added, and the resultant mixture was stirred at room temperature for 24 hours to effect the alkylation reaction. The resulting reaction solution was then added dropwise to 100 ml of a 5% aqueous solution of potassium hydrogen sulfate, followed by extraction with 100 ml of chloroform. The chloroform layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. Tetrahydrofuran (10 ml), a 10% aqueous solution of sodium hydroxide (2.0 ml) and methanol (4.0 ml) were added successively to the resultant residue to dissolve the latter. The solution obtained was left over at room temperature for 24 hours. The resulting reaction solution was concentrated under reduced pressure, and the residue was extracted with 100 ml of chloroform. The extract was washed successively with a 5% aqueous solution of potassium hydrogen sulfate and water, and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column {gradiently developed with chloroform →chloroform-ethanol (50:1)} to give 89.6 mg of 3-n-hexyloxy-4-n-hexyloxymethylbenzoic acid as pale yellowish needles (which were in the crystalline form in refrigerator but became an oil at room temperature). EIMS: m/z 336 (M+).
0-isopropylidene-3-hydroxy-4-hydroxymethylbenzoic acid[ No CAS ]
O-isopropylidene-3-hydroxy-4-hydroxymethylbenzoic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium bicarbonate; potassium hydrogen sulphate; pyridinium p-toluenesulfonate In acetone
20 Preparation of 0-isopropylidene-3-hydroxy-4-hydroxymethylbenzoic acid
EXAMPLE 20 Preparation of 0-isopropylidene-3-hydroxy-4-hydroxymethylbenzoic acid Acetone (2.0 ml) was added to 100 mg of 3-hydroxy-4-hydroxymethylbenzoic acid to dissolve the latter compound. Thereafter, 15.0 mg of pyridinium p-toluenesulfonate and 68 μl of 2-methoxypropene were added. The resultant mixture was left over at room temperature for 24 hours. The reaction solution obtained was added dropwise to 10 ml of a saturated aqueous solution of sodium hydrogen carbonate. The resulting mixture was concentrated under reduced pressure to remove acetone therefrom. The remaining aqueous phase was washed with chloroform, and then mixed with a 5% aqueous solution of potassium hydrogen sulfate to adjust the pH to 3-4. The resultant solution was extracted twice with 10 ml of chloroform, and the chloroform extract was dried over anhydrous sodium sulfate. The chloroform solution was concentrated under reduced pressure, and the residue was purified by preparative thin layer chromatography {developer: chloroform-methanol (10:1)} to give 74.3 mg of O-isopropylidene-3-hydroxy-4-hydroxymethylbenzoic acid as a white solid. Melting point: 153-156° C. EIMS: m/z 208 (M+).
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