Hydrochloric Acid → N-(2-hydroxyethyl)-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzamide

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Reaction Conditions

Reaction Steps

In 50 ml of n-octane was dissolved 2.00 g (6.9 mmol) of 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid, and 5.0 ml (35 mmol) of thionyl chloride was added to the solution, followed by heating at 90° C. for 5 hours to conduct a reaction. After completion of the reaction, the reaction mixture was cooled, and n-octane was removed by evaporation. The residue was dissolved in n-octane, and a pyridine solution of 0.84 g (13.8 mmol) of 2-hydroxyethylamine was added thereto dropwise at room temperature. After the dropwise addition, the mixture was stirred for 10 minutes, poured into a 12% hydrochloric acid aqueous solution, and extracted with ethyl acetate. The organic layer was washed with water and then with a saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The resulting crude product was recrystallized from an ethyl acetate/hexane mixed solvent to obtain 0.50 g (yield: 22%) of N-(2-hydroxyethyl)-4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzamide represented by the following structural formula (hereinafter referred to as compound 46) as white crystals. The analytical results are shown below. ##STR67##

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