Sodium Hydroxide → p-Benzyloxy-(1-methylheptyloxy)benzene

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Reaction Steps

Hydroquinone monobenzyl ether (50 g, 0.25 mol) was added to ethanol (250 ml), followed by adding to the solution, NaOH (12 g, 0.30 mol) and optically active p-toluenesulfonic acid 1-methyl-heptyl ester (78 g, 0.274 mol) prepared in Example 1 with stirring, refluxing the mixture for about 10 hours, distilling off ethanol, adding 6N-HCl (250 ml) and toluene (500 ml) to carry out extraction with toluene, washing the toluene layer with 2N-NaOH aqueous solution, then with water till the washing water became neutral, and distilling off the solvent to obtain optically active p-(1-methyl-heptyloxy)-phenol benzyl ether (76 g). This product (50 g, 0.16 mol) was dissolved in ethanol (100 ml) and reduced in the presence of Pd/C catalyst to obtain optically active p-(1-methylheptyloxy)-phenol (24 g) having a b.p. of 162°-165° C./6 mmHg.

Provenance & Evidence