Propylene Oxide → 3,5-Bis(1,1-dimethylethyl)-4-hydroxy-β-methylbenzeneethanol

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Reaction Steps

To a stirred slurry of 66.7 g (0.5 mole) aluminum chloride in 250 ml toluene, 103.0 g (0.5 mole) 2,6-di-tert-butylphenol dissolved in 250 ml toluene was slowly added through a dropping funnel under a nitrogen atmosphere and under dry ice/acetone bath cooling so as to maintain the temperature of the mixture at -25° C. to -20° C. The addition was complete in 10 minutes. To the resulting orange-yellow slurry, 87.0 g (1.5 mole) propylene oxide dissolved in 250 ml toluene dropwise with stirring was slowly added over a period of 1.5 hours while maintaining the temperature at -35° C. to -30° C. After stirring for an additional 0.5 hours, the mixture was worked up as described in Example 1 to give 21.2 g (16% yield) of the desired product as colorless needles. This product proved identical to that obtained in Example 1 based on IR and NMR analysis.

Provenance & Evidence