Organic Syntheses, CV 1, 494
Submitted by Harold Hibbert and Pauline Burt.
Checked by Roger Adams and F. E. Kendall.
1. Procedure
To a solution of
42 g. (0.30 mole) of perbenzoic acid (p. 431) in
500 cc. of chloroform is added
30 g. (0.29 mole) of styrene (b.p.
141–143°)
(p. 440). The solution is kept at 0° for twenty-four hours and is shaken frequently during the first hour. At the end of twenty-four hours, titration of an aliquot part of the solution shows that only the slight excess of
perbenzoic acid remains (Note
1).
The
benzoic acid is removed from the
chloroform solution by shaking with an excess of
10 per cent sodium hydroxide solution, the alkali is removed by washing with water, and the
chloroform solution is dried with anhydrous
sodium sulfate. It is then fractionated through an
efficient distilling column (p. 130). Removal of the
chloroform leaves a practically colorless liquid which distils at
188–192° (uncorr.) (Note
2). The yield is
24–26 g. (
69–75 per cent of the theoretical amount).
2. Notes
2. If the
styrene oxide is distilled over a free flame some decomposition takes place as indicated by the formation of water. This is not observed if the product is distilled from an
oil bath.
3. Discussion
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