In a
2-l. round-bottomed flask fitted with a
mechanical stirrer is placed a solution of
70 g. (1.75 moles) of sodium hydroxide in 400 cc. of water. To this solution is then added
230 g. (1.71 moles) of 2-chlorocyclohexanol (p. 158). The mixture is stirred vigorously for about one hour (Note
1). The stirring is then stopped and the upper layer is separated and fractionated carefully through an
efficient column.
The fractions collected are 100–129°, 129–134°, and 134–175° (Note
2). The first fraction is mainly
cyclohexene oxide but contains some water which is separated with a
separatory funnel before the second fractionation. After the fraction boiling at
100–129° is collected, the
condenser should be removed and dried thoroughly before collecting the second fraction, in order to insure anhydrous material. After two or three fractionations, the yield of
cyclohexene oxide boiling at
129–134° is
117–122 g. (
70–73 per cent of the theoretical amount).