Sodium Hydroxide → 2-{2-[(3-Methyloxiran-2-yl)methoxy]phenyl}ethan-1-ol

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Reaction Steps

A mixture of 5.04 g (0.033 mole) of 2-(2-hydroxyethyl)-3-methylphenol, 1.33 g (0.033 mole) of sodium hydroxide in 135 ml of water, and 5.00 g (0.033 mmole) of erythro-(1-bromoethyl)oxirane in 25 ml of 1,2-dimethoxyethane was stirred at room temperature for about 72 hours. The mixture was extracted with 5×100 ml of ether. The extract was washed with dilute sodium hydroxide solution, dilute brine and saturated brine, dried over MgSO4 and concentrated in vacuo to give 4.25 g (58%) of 2-methyl-3-[2-(2-hydroxyethyl)phenoxymethyl]oxirane. A 1:1 (v/v) mixture of 1-methylethylamine and water (130 ml) was added to the oxirane and the mixture was heated at reflux for 5 hours, and concentrated in vacuo to dryness. The residue was dissolved in ether, dried over MgSO4 and concentrated to dryness to give 2.90 g of oil. The oil was flash chromatographed on a silica gel column by elution with 3% CH3OH in CHCl3 saturated with ammonia gas to give 0.5 g of product. Conversion to the oxalate salt gave material with m.p. 138°-140° C. (0.5 isopropanol solvate).

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