Water → (2RS,3RS)-3-(2-Ethoxyphenoxy)-1,2-dihydroxy-3-phenylpropane

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Water (800 mL), sodium hydroxide (50%, 83.1 mL), tributylmethyl-ammonium chloride (75%, 27.5 ml), and 2-ethoxyphenol (306.72 g) were combined and stirred at 20-25° C. The methylene chloride solution of 2,3-epoxy-3-phenylpropanol from Example 1 was added, and the two phase mixture was stirred and heated to 40° C. internal temperature. The methylene chloride was distilled at atmospheric pressure over a 3-4 hour period. When the methylene chloride had been removed, the internal temperature was raised to 60° C. for 2 hours. The mixture was cooled to below 30° C., toluene (1200 ml) was added, and the mixture was stirred for 5 minutes. The phases were separated and the aqueous phase was extracted with toluene (800 mL). The toluene solutions were combined and washed with 1 N NaOH (2×400 ml) and with water (400 mL) at approximately 25° C. The toluene solution was concentrated under partial vacuum maintaining an internal temperature of 40-50° C. The residual oil was dissolved in methyl t-butyl ether (760 ml), and water content was verified to be less than 0.1% by potassium fluoride assay. The solution was seeded with crystals of the title compound at 20-25° C., stirred for 1 hour, and cooled to 0° C. for 2 hours. The resulting solids were filtered, washed with methyl t-butylether (2×200 mL, cooled to −15° C.), and dried under vacuum to yield 256.1 g of the title compound (60.5% from cinnamyl alcohol).

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