Toluene → (S)-1-butyloxy-2-(p-toluenesulfonyloxy)propane

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Reaction Steps

A mixture of this (S)-1-butyloxy-2-hydroxypropane (47.6 g, 0.36 mol) with anhydrous pyridine (300 g) was cooled with ice, followed by dropwise adding thereto a solution of p-toluenesulfonyl chloride (75.8 g, 0.20 mol) in pyridine (70 ml) at 0° C., agitating the mixture at room temperature for 3 hours, adding toluene (800 ml), agitating the mixture, several times washing the resulting organic layer with water, drying it over anhydrous magnesium sulfate and distilling off toluene to obtain (S)-1-butyloxy-2-(p-toluenesulfonyloxy)propane (93.1 g). A solution of 4-hydroxy-4'-octyloxybiphenyl (10 g, 0.017 mol) in THF (20 ml) was dropwise added to a mixture of sodium hydride (0.85 g, 0.035 mol) with THF (10 ml), followed by further dropwise adding a solution of the above (S)-1-butyloxy-2-(p-toluenesulfonyloxy)-propane (5.7 g, 0.02 mol) in DMF (10 ml), agitating the mixture at 60° C. for 4 hours, allowing it to cool down, adding toluene, agitating the mixture, washing with 6N-HCl, then with 2N-NaOH aqueous solution and further with water, drying over anhydrous magnesium sulfate, distilling off toluene and recrystallizing the residue from ethanol (100 ml) to obtain (R)-4-(2'-butyloxy-1'-methyl)ethyloxy-4'-octyloxybiphenyl (8.2 g) (m.p. 39.6° C.).

Provenance & Evidence