A
1-L, four-necked flask is fitted with a
nitrogen inlet tube,
stirrer,
dropping funnel, and
thermometer.
Acetic acid (558 g) is introduced and
107.6 g (0.439 mol) of manganese acetate tetrahydrate (Note
1) is added with stirring and heating under
nitrogen. When the temperature reaches 90°C,
16.5 g of solid potassium permanganate (0.104 mol) is added. After the temperature has again fallen to 90°C,
175 mL (189 g, 1.86 mol) of acetic anhydride (Note
2) is added. When the temperature rise has ceased,
44.0 g of 1-decene (0.312 mol) (Note
3) is introduced, followed at once by
250 g of anhydrous sodium acetate. The reaction mixture is then heated to reflux (134°C pot temperature). After 2 hr of reflux under
nitrogen the reaction mixture, now clear yellow, is diluted with 1 L of water. The crude product is extracted into
200 mL of benzene, and the aqueous layer again washed with
100 mL of benzene.
Benzene is distilled from the combined extracts to give
55.1 g of lactone and
1-decene.
1-Decene is removed by vacuum distillation, followed by the lactone, which distills at
98–99°C (0.05 mm) (Note
4). The yield of
γ-(n-octyl)-γ-butyrolactone is
34.1 g (
66% based on
potassium permanganate. However, the lactone yield based on olefin consumed is greater than
95%.)