Ethanol → Bis(2-methylbutyl) ether

Participants

Reaction Conditions

Reaction Steps

Next, into a solution obtained by dissolving hydroquinone (248 g) and potassium hydroxide (88 g) in water (30 ml) and ethanol (2 l) was added the above p-toluenesulfonic acid 2-methylbutyl ester (366 g) and the mixture was heated with stirring at 60° C. for 2 hours and then under reflux for 7 hours, followed by distilling off ethanol (1.7 l), adding water (1.9 l) and 6N hydrochloric acid for acidification to separate a brown oily substance, extracting this substance with heptane (150 ml), water-washing the resulting heptane layer, distilling it under reduced pressure to obtain a fraction of b.p. 115°~135° C.(2.5 mmHg) (176 g), dissolving this fraction in heptane (300 ml), subjecting the solution to extraction with 1N aqueous solution of KOH (1 l), washing the resulting extract liquid with heptane (100 ml), adding 6N hydrochloric acid to the alkaline aqueous layer for acidification to separate an oily substance, water-washing this substance, and distilling it under reduced pressure to obtain a fraction of b.p. 107°~111° C. (2 mmHg) (140 g), dissolving this fraction in hexane (200 ml), and keeping the solution at 0° C. for crystal deposition to obtain optically active hydroquinonemono (2-methylbutyl) ether (m.p. 41°~42° C.) (129 g).

Provenance & Evidence