Potassium Hydroxide → 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid

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Reaction Steps

In methanol was dissolved 18.1 g (59.5 mmol) of methyl 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoate, and 30 ml of an aqueous solution of 8.35 g (148 mmol) of potassium hydroxide was added thereto, followed by heating under reflux for 5 hours. Methanol was evaporated, and a 12% hydrochloric acid aqueous solution added to the residue, followed by extraction with ethyl acetate. The organic layer was washed successively with water and a saturated aqueous solution of sodium chloride and dried over sodium sulfate, followed by concentration. The resulting crude product was recrystallized from an ethyl acetate/hexane mixed solvent to obtain 13.06 g (yield: 75%) of 4-{(2E)-3,7-dimethylocta-2,6-dienyloxy}-2-hydroxybenzoic acid represented by the following structural formula (hereinafter referred to as compound 39) as white crystals. The analytical results are shown below. ##STR60##

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