Organic Syntheses, CV 3, 187
Submitted by Martin E. Synerholm
Checked by Arthur C. Cope and James J. Ryan.
1. Procedure
In a
200-ml. round-bottomed flask fitted with an
efficient reflux condenser are mixed
31.4 ml. (38 g., 0.27 mole) of freshly distilled benzoyl chloride,
28.2 ml. (25 g., 0.35 mole) of tetrahydrofuran (Note
1), and
5 g. of freshly fused zinc chloride. A vigorous reaction begins immediately, and after a few seconds, when the mixture starts to boil, external cooling is applied with an
ice bath. After the initial reaction has subsided, the mixture is heated on a
steam bath for 15 minutes, cooled, and dissolved in
100 ml. of benzene. The
benzene solution is washed with
100 ml. of a 5% solution of sodium chloride and then with
100 ml. of a saturated solution of sodium bicarbonate. The
benzene layer is dried over anhydrous
sodium sulfate and fractionally distilled from a modified
Claisen flask.
The product is collected at 140–143°/5 mm., 132–135°/2.5 mm.;
nD25 1.5176 (Note
2). The yield is
45–48 g. (
78–83%).
2. Notes
1. Good-quality commercial
tetrahydrofuran may be used as received, or redistilled; b.p.
65–66°.
2. The product develops a slight yellow tint on standing.
3. Discussion
Copyright © 1921-2002, Organic Syntheses, Inc. All Rights Reserved