Org. Synth. 1925, 5, 35
DOI: 10.15227/orgsyn.005.0035
[Cyclohexane, 1,2-epoxy-]
Submitted by A. E. Osterberg
Checked by C. S. Marvel and A. B. Adams.
1. Procedure
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).
2. Notes
1. If the stirring is continued for much longer than one and one-half hours, the yield may be lessened somewhat.
2. There is a slight high-boiling residue which begins to decompose if the temperature is raised above this point. The products of decomposition are hard to remove from the distilling flask.
3. Discussion
Cyclohexene oxide can be prepared from 2-iodocyclohexanol1 or 2-chlorocyclohexanol2 and alkalies; and by the oxidation of cyclohexene with perbenzoic acid.3
This preparation is referenced from:

References and Notes
  1. Brunel, Compt. rend. 136, 384 (1903); 137, 62 (1903); Bull. soc. chim. (3) 29, 883 (1903).
  2. Godchot and Bedos, Bull. soc. chim. (4) 37, 1454 (1925).
  3. Godchot and Bedos, Compt. rend. 174, 462 (1922).

Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)

sodium hydroxide (1310-73-2)

Cyclohexene (110-83-8)

2-Chlorocyclohexanol (1561-86-0)

Cyclohexene oxide,
Cyclohexane, 1,2-epoxy- (286-20-4)


Perbenzoic acid (93-59-4)